Three decades of unveiling the complex chemistry of C-nitroso species with computational chemistry

Bianchi, Pauline; Monbaliu, Jean-Christophe

doi:10.1039/d1qo01415c

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Three decades of unveiling the complex chemistry of C-nitroso species with computational chemistry

Bianchi, Pauline; Monbaliu, Jean-Christophe

2022 • In Organic Chemistry Frontiers, 9, p. 223-264

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https://hdl.handle.net/2268/265093

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10.1039/d1qo01415c

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Keywords :

Computational Chemistry; Organic Chemistry; Nitroso species

Abstract :

[en] C-Nitroso species are characterized by a unique nitrogen–oxygen combination located next to a carbon backbone, which confers them a unique ambiphilic and high reactivity towards nucleophilic, electrophilic but also radical species. Although this ambivalence can be seen as a strong asset for developing versatile synthetic aminohydroxylation and/or hydroxylamination processes mainly through nitroso Diels–Alder, nitroso ene, and nitrosoaldol reactions, it also contributes to complex optimization and rationalization arising from the many competitive pathways, that is, the occurrence of regioisomers and stereoisomers, as well as dimerization and tautomerization side-reactions. Complex reactivity profiles are usually seen by synthetic organic chemists as major hurdles to overcome, despite the armada of analytical and purification methods available to them, and hence to achieve selective and exploitable developments of such reactions. The rise of computational chemistry and resources has certainly changed their perspectives, since it provides a very different angle to gather insights on intrinsic properties, reactivity, and mechanisms. In silico chemistry also provides a robust alternative to time and resource-consuming synthetic work and can therefore contribute to alleviate wasteful preparations by guiding the chemist toward the best combination of reagents to achieve high selectivity and yield. The synergistic combination of synthetic organic chemistry and computational chemistry, within the specific context of the complex chemistry of C-nitroso species, is discussed in this work. This review aims at giving an overview of the molecular and chemical properties obtained through computational chemistry as an enabling support for the rationalization and optimization of reactions relying on ambiphilic C-nitroso species over the 3 last decades. It provides clear, concise, and illustrated guidelines for the synthetic chemist in search of inspiration through computations.

Research Center/Unit :

MolSys - Molecular Systems - ULiège

Disciplines :

Chemistry

Author, co-author :

Bianchi, Pauline ; Université de Liège - ULiège > Département de chimie (sciences) > CITOS

Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Département de chimie (sciences) > CITOS

Language :

English

Title :

Three decades of unveiling the complex chemistry of C-nitroso species with computational chemistry

Publication date :

2022

Journal title :

Organic Chemistry Frontiers

ISSN :

2052-4110

eISSN :

2052-4129

Publisher :

Royal Society of Chemistry, United Kingdom

Volume :

Pages :

223-264

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://doi.org/10.1039/D1QO01415C

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique

Available on ORBi :

since 18 November 2021

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Bibliography

J. Lee L. Chen A. H. West G. B. Richter-Addo Interactions of organic nitroso compounds with metals Chem. Rev. 2002 102 1019
G. W. Kirby, Electrophilic C-nitroso-compounds, Chem. Soc. Rev., 1977, 6, 1
B. G. Gowenlock G. B. Richter-Addo Preparations of C-nitroso compounds Chem. Rev. 2004 104 3315
H. Yamamoto N. Momiyama Rich chemistry of nitroso compounds Chem. Commun. 2005 3514
D. Gooden H. Chakrapani E. Toone C-Nitroso Compounds: Synthesis, Physicochemical Properties and Biological Activities Curr. Top. Med. Chem. 2005 5 687
I. M. Lyapkalo S. L. Ioffe Conjugated nitrosoalkenes Russ. Chem. Rev. 1998 67 467
I. Biljan H. Vančik Aromatic C-nitroso compounds and their dimers: A model for probing the reaction mechanisms in crystalline molecular solids Crystals 2017 7 376
S. Iwasa A. Fakhruddin H. Nishiyama Synthesis of Acylnitroso Intermediates and Their Synthetic Applications Mini-Rev. Org. Chem. 2005 2 157
L. I. Palmer C. P. Frazier J. R. de Alaniz Developments in nitrosocarbonyl chemistry: Mild oxidation of N-substituted hydroxylamines leads to new discoveries Synthesis 2014 269
M. G. Memeo P. Quadrelli Generation and Trapping of Nitrosocarbonyl Intermediates Chem. Rev. 2017 117 2108
P. Merino T. Tejero I. Delso R. Matute Recent Advances on Asymmetric Nitroso Aldol Reaction Synthesis 2016 653
S. Dana I. Ramakrishna M. Baidya Ambident Reactivity of Nitroso Compounds for Direct Amination and Hydroxylation of Carbonyls Synthesis 2017 3281
D. Beaudoin J. D. Wuest Dimerization of Aromatic C-Nitroso Compounds Chem. Rev. 2016 116 258
L. R. Domingo M. Ríos-Gutiérrez E. Chamorro P. Pérez Aromaticity in Pseudocyclic Transition State Structures? A Critical Rationalisation Based on the Topological Analysis of Electron Density ChemistrySelect 2016 1 6026
L. R. Domingo M. Ríos-Gutiérrez B. Silvi P. Pérez The Mysticism of Pseudocyclic Reactions: A Contemporary Rationalisation of Organic Reactivity Based on Electron Density Analysis Eur. J. Org. Chem. 2018 1107
Y. Yamamoto H. Yamamoto Recent advances in asymmetric nitroso Diels-Alder reactions Eur. J. Org. Chem. 2006 2031
B. S. Bodnar M. J. Miller The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses Angew. Chem., Int. Ed. 2011 50 5630
S. Carosso M. J. Miller Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products Org. Biomol. Chem. 2014 12 7445
L. Brulíková A. Harrison M. J. Miller J. Hlaváč Stereo-and regioselectivity of the hetero-Diels-Alder reaction of nitroso derivatives with conjugated dienes Beilstein J. Org. Chem. 2016 12 1949
A. Menichetti F. Berti M. Pineschi Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity Molecules 2020 25 563
W. Adam O. Krebs The Nitroso Ene Reaction: A Regioselective and Stereoselective Allylic Nitrogen Functionalization of Mechanistic Delight and Synthetic Potential Chem. Rev. 2003 103 4131
M. Baidya H. Yamamoto Advancements in the nascent nitroso-ene reaction Synthesis 2013 1931
Y. Gao S. Yang W. Xiao J. Nie X. Q. Hu Radical chemistry of nitrosoarenes: Concepts, synthetic applications and directions Chem. Commun. 2020 56 13719
L. D. Ardila-Leal R. A. Poutou-Piñales A. M. Pedroza-Rodríguez B. E. Quevedo-Hidalgo A brief history of colour, the environmental impact of synthetic dyes and removal by using laccases Molecules 2021 26 3813
R. Raue and J. F. Corbett, Nitro and nitroso dyes, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, 2000
J. E. T. Corrie G. W. Kirby J. W. M. Mackinnon Reactions of Transient C-Nitrosocarbonyl Compounds with Dienes, Mono-olefins, and Nucleophiles J. Chem. Soc., Perkin Trans. 1 1985 883
I. Novak Computational thermochemistry of C-nitroso compounds Struct. Chem. 2016 27 1395
V. E. H. Kassin R. Morodo T. Toupy I. Jacquemin K. Van Hecke R. Robiette J. C. M. Monbaliu A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones Green Chem. 2021 23 2336
J. F. Arenas J. C. Otero D. Peláez J. Soto CASPT2 study of the decomposition of nitrosomethane and its tautomerization reactions in the ground and low-lying excited states J. Org. Chem. 2006 71 983
S. Pou D. E. Anderson W. Surichamorn L. L. Keaton M. L. Tod Biological studies of a nitroso compound that releases nitric oxide upon illumination Mol. Pharmacol. 1994 46 709
A. Di Stilo C. Medana B. Ferrarotti A. L. Gasco D. Ghigo A. Bosia P. A. Martorana A. Gasco In vitro and in vivo vasodilating activity of nitroso derivatives gem-substituted with electron-withdrawing groups Pharmacol. Res. 2000 41 469
N. A. Magnus S. Campagna P. N. Confalone S. Savage D. J. Meloni R. E. Waltermire R. G. Wethman M. Yates Quaternary chiral center via diastereoselective enolate amination enables the synthesis of an anti-inflammatory agent Org. Process Res. Dev. 2010 14 159
N. Emmanuel P. Bianchi J. Legros J. C. M. Monbaliu A safe and compact flow platform for the neutralization of a mustard gas simulant with air and light Green Chem. 2020 22 4105
E. Schrödinger An undulatory theory of the mechanics of atoms and molecules Phys. Rev. 1926 28 1049
M. Born R. J. Oppenheimer Zur Quamtentheorie der Molekeln Ann. Phys. 1927 20 457
D. R. Hartree The Wave Mechanics of an Atom with a Non-Coulomb Central Field Part I Theory and Methods Math. Proc. Cambridge Philos. Soc. 1928 24 89
J. C. Slater The self consistent field and the structure of atoms Phys. Rev. 1928 32 339
C. C. J. Roothaan New developments in molecular orbital theory Rev. Mod. Phys. 1951 23 69
B. O. Roos The Complete Active Space Self-Consistent Field Method and its Applications in Electronic Structure Calculations Adv. Chem. Phys. 1987 69 399
J. Čížek On the Correlation Problem in Atomic and Molecular Systems. Calculation of Wavefunction Components in Ursell-Type Expansion Using Quantum-Field Theoretical Methods J. Chem. Phys. 1966 45 4256
M. S. Plesset C. Møller Note on an Approximation Treatment for Many-Electron Systems Phys. Rev. 1934 46 618
K. Andersson P. Å. Malmqvist B. O. Roos Second-order perturbation theory with a complete active space self-consistent field reference function J. Chem. Phys. 1992 96 1218
J. A. Pople M. Head-Gordon D. J. Fox K. Raghavachari L. A. Curtiss Gaussian-1 theory: A general procedure for prediction of molecular energies J. Chem. Phys. 1989 90 5622
J. A. Montgomery M. J. Frisch J. W. Ochterski G. A. Petersson A complete basis set model chemistry. VI. Use of density functional geometries and frequencies J. Chem. Phys. 1999 110 2822
P. Hohenberg W. Kohn Inhomogeneous Electron Gas Phys. Rev. 1964 136 864
W. Kohn L. J. Sham Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. 1965 140 1133
J. P. Perdew K. Schmidt Jacob's ladder of density functional approximations for the exchange-correlation energy AIP Conf. Proc. 2001 577 1
N. Mardirossian M. Head-Gordon How Accurate Are the Minnesota Density Functionals for Noncovalent Interactions, Isomerization Energies, Thermochemistry, and Barrier Heights Involving Molecules Composed of Main-Group Elements? J. Chem. Theory Comput. 2016 12 4303
N. Mardirossian M. Head-Gordon Thirty years of density functional theory in computational chemistry: An overview and extensive assessment of 200 density functionals Mol. Phys. 2017 115 2315
L. Goerigk A. Hansen C. Bauer S. Ehrlich A. Najibi S. Grimme A look at the density functional theory zoo with the advanced GMTKN55 database for general main group thermochemistry, kinetics and noncovalent interactions Phys. Chem. Chem. Phys. 2017 19 32184
S. Grimme Accurate description of van der Waals complexes by density functional theory including empirical corrections J. Comput. Chem. 2004 25 1463
E. Runge E. K. U. Gross Density-Functional Theory for Time-Dependent Systems Phys. Rev. Lett. 1984 52 997
R. Ditchfield W. J. Hehre J. A. Pople Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules J. Chem. Phys. 1971 54 724
T. H. Dunning Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen J. Chem. Phys. 1989 90 1007
L. Onsager Electric Moments of Molecules in Liquids J. Am. Chem. Soc. 1936 58 1486
S. Miertuš E. Scrocco J. Tomasi Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects Chem. Phys. 1981 55 117
A. V. Marenich C. J. Cramer D. G. Truhlar Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 2009 113 6378
H. B. Schlegel Optimization of Equilibrium Geometries and Transition Structures J. Comput. Chem. 1982 3 214
H. B. Schlegel Exploring potential energy surfaces for chemical reactions: An overview of some practical methods J. Comput. Chem. 2003 24 1514
C. Gonzalez H. B. Schlegel Reaction path following in mass-weighted internal coordinates J. Phys. Chem. 1990 94 5523
R. S. Mulliken Electronic Population Analysis on LCAO-MO Molecular Wave Functions. I J. Chem. Phys. 1955 23 1833
A. E. Reed R. B. Weinstock F. Weinhold Natural population analysis J. Chem. Phys. 1985 83 735
R. F. W. Bader C. F. Matta Atoms in molecules as non-overlapping, bounded, space-filling open quantum systems Found. Chem. 2013 15 253
G. J. Cheng X. Zhang L. W. Chung L. Xu Y. D. Wu Computational organic chemistry: Bridging theory and experiment in establishing the mechanisms of chemical reactions J. Am. Chem. Soc. 2015 137 1706
P. Nakliang S. Yoon S. Choi Emerging Computational Approaches for the Study of Regio-and Stereoselectivity in Organic Synthesis Org. Chem. Front. 2021 8 5165 5181
J. A. Keith V. Vassilev-Galindo B. Cheng S. Chmiela M. Gastegger K.-R. Müller A. Tkatchenko Combining Machine Learning and Computational Chemistry for Predictive Insights Into Chemical Systems Chem. Rev. 2021 121 9816
Z. Lin Interplay between theory and experiment: Computational organometallic and transition metal chemistry Acc. Chem. Res. 2010 43 602
D. Chen Q. Xie J. Zhu Unconventional Aromaticity in Organometallics: The Power of Transition Metals Acc. Chem. Res. 2019 52 1449
L. R. Domingo M. Ríos-Gutiérrez P. Pérez Applications of the Conceptual Density Functional Theory Indices to Organic Chemistry Reactivity Molecules 2016 21 748
P. Geerlings E. Chamorro P. K. Chattaraj F. De Proft J. L. Gázquez S. Liu C. Morell A. Toro-Labbé A. Vela P. Ayers Conceptual density functional theory: status, prospects, issues Theor. Chem. Acc. 2020 139 1
E. Scrocco J. Tomasi The electrostatic molecular potential as a tool for the interpretation of molecular properties Fortschr. Chem. Forsch. 1973 42 95
P. Politzer R. Bar-Adon Computational Analysis of the Reactive Properties of Some Nitrosoaromatic Molecules J. Phys. Chem. 1987 91 2069
R. G. Parr W. Yang Density Functional Approach to the Frontier-Electron Theory of Chemical Reactivity J. Am. Chem. Soc. 1984 106 4049
W. Yang W. J. Mortier The Use of Global and Local Molecular Parameters for the Analysis of the Gas-Phase Basicity of Amines J. Am. Chem. Soc. 1986 108 5708
V. Pilepić S. Uršić Nucleophilic reactivity of the nitroso group. Fukui function DFT calculations for nitrosobenzene and 2-methyl-2-nitrosopropane J. Mol. Struct.: THEOCHEM 2001 538 41
R. K. Roy S. Krishnamurti P. Geerlings S. Pal Local softness and hardness based reactivity descriptors for predicting intra-and intermolecular reactivity sequences: Carbonyl compounds J. Phys. Chem. A 1998 102 3746
K. Senthilkumar P. Kolandaivel Post Hartree-Fock and density functional theory studies on structure and conformational stability of nitrosoethylene and substituted compounds of nitrosoethylene Comput. Chem. 2002 26 207
R. Kanakaraju P. Kolandaivel B. G. Gowenlock Quantum chemical studies of nitrosobuta-1,3-diene and nitrosostyrene molecules J. Mol. Struct.: THEOCHEM 2002 577 121
K. Anandan P. Kolandaivel R. Kumaresan B. G. Gowenlock Ab initio and DFT studies on structure and stability of nitroso and nitro substituted furan molecules J. Mol. Struct.: THEOCHEM 2003 639 213
K. Anandan P. Kolandaivel R. Kumaresan B. G. Gowenlock Quantum chemical studies on structure, conformation and isomerization of nitroso, nitro substituted benzene and 1,3-cyclopentadiene J. Mol. Struct.: THEOCHEM 2004 680 149
S. Vijayakumar P. Kolandaivel Isomerization of C3H3NO isomers: Ab initio study Mol. Phys. 2006 104 1401
L. R. Domingo M. J. Aurell P. Pérez R. Contreras Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions Tetrahedron 2002 58 4417
L. R. Domingo M. J. Aurell P. Pérez R. Contreras Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions Tetrahedron 2002 58 4417
L. R. Domingo E. Chamorro P. Pérez Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study J. Org. Chem. 2008 73 4615
L. R. Domingo A new C-C bond formation model based on the quantum chemical topology of electron density RSC Adv. 2014 4 32415
L. R. Domingo P. Pérez J. A. Sáez Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions RSC Adv. 2013 3 1486
W. Neugebauer C. Sessa C. Steuer T. Allscher H. Stege Naphthol Green-a forgotten artists' pigment of the early 20th century. History, chemistry and analytical identification J. Cult. Herit. 2019 36 153
S. Lacombe M. Loudet A. Dargelos J. M. Camou Calculation of the electronic and photoelectronic spectra of nitroso compounds: A reinvestigation by use of configuration interaction methods Chem. Phys. 2000 258 1
E. K. Dolgov V. A. Bataev V. I. Pupyshev I. A. Godunov Ab initio description of the structure and dynamics of the nitrosomethane molecule in the first excited singlet and triplet electronic states Int. J. Quantum Chem. 2004 96 589
H. M. Badawi W. Förner Study of structural stability and vibrational spectra of nitroso and nitroketenes J. Mol. Struct.: THEOCHEM 2001 542 7
H. M. Badawi A. A. El-Rayyes Vibrational spectra and potential energy distributions of normal modes of 3-nitroso-and 3-nitrocyclopropenes J. Mol. Struct.: THEOCHEM 2002 588 17
H. M. Badawi W. Förner Analyses of vibrational spectra of nitroso-and nitroethylenes J. Mol. Struct.: THEOCHEM 2004 677 153
W. Förner H. M. Badawi Infrared and Raman spectra and vibrational analyses calculated with Moeller-Plesset perturbation theory of second order of nitrosoethylene and its chloro-derivatives J. Mol. Model. 2005 11 542
H. M. Badawi W. Förner Influence of fluorine substitution in nitrosoethylene and their vibrational spectra, calculated with Møller-Plesset perturbation theory of second order J. Mol. Struct.: THEOCHEM 2005 725 183
D. Jacquemin E. A. Perpète The n → π∗ transition in nitroso compounds: A TD-DFT study Chem. Phys. Lett. 2006 420 529
N. A. Hussien A. M. Mohammed M. Tessema F. B. Dejene M. Redi-Abshiro Solvent polarity and excitation wavelength dependence of the dual fluorescence in N,N-diethyl-4-nitrosoaniline J. Fluoresc. 2012 22 451
E. Procházková L. Čechová J. Tarábek Z. Janeba M. Dračínský Tunable Push-Pull Interactions in 5-Nitrosopyrimidines J. Org. Chem. 2016 81 3780
V. Ragavendran S. Muthunatesan An insight into the conformal flexibility and vibrational behavior of 2-nitroso-1-naphthol: A density functional theory approach Spectrosc. Lett. 2016 49 294
C. Azarias C. Habert Š. Budzák X. Blase I. Duchemin D. Jacquemin Calculations of n→π∗ Transition Energies: Comparisons between TD-DFT, ADC, CC, CASPT2, and BSE/GW Descriptions J. Phys. Chem. A 2017 121 6122
U. Banerjee W. L. Karney B. S. Ault A. D. Gudmundsdottir Photolysis of 5-azido-3-phenylisoxazole at cryogenic temperature: Formation and direct detection of a nitrosoalkene Molecules 2020 25 543
R. H. Cox M. Hamada A 13C NMR investigation of restricted rotation and dimerization in p-substituted nitrosobenzenes Org. Magn. Reson. 1979 12 322
M. Azoulay E. Fischer Low-temperature Proton Nuclear Magnetic Resonance and Ultraviolet Absorption Spectra and Photochemistry of the System Nitrosobenzene-Azodioxybenzene and its Methyl Derivatives J. Chem. Soc., Perkin Trans. 2 1982 637
K. Varga I. Biljan V. Tomišić Z. Mihalić H. Vančik Quantum Chemical Calculations of Monomer-Dimer Equilibria of Aromatic C-Nitroso Compounds J. Phys. Chem. A 2018 122 2542
R. Glaser R. K. Murmann C. L. Barnes Why do nitroso compounds dimerize while their oxime tautomers do not? A structural study of the trans-dimer of 2-chloro-2-methyl-3-nitrosobutane and higher level ab initio study of thermodynamic stabilities and electronic structures of isomers of diazene J. Org. Chem. 1996 61 1047
I. Rončević P. Bibulić H. Vančik I. Biljan Solution equilibria of aromatic dinitroso compounds: a combined NMR and DFT study Struct. Chem. 2018 29 1489
A. Kržan J. Mavri Nitroso-naphthol quinone-monooxime tautomeric equilibrium revisited: Evidence for oximo group isomerization Chem. Phys. 2002 277 71
V. Enchev G. Ivanova A. Ugrinov G. D. Neykov S. Minchev N. Stoyanov Ab initio quantum chemical and NMR study of the symmetric monooximes of 1,2,3-phenalenetrione and 1,2,3-indantrione J. Mol. Struct. 1998 440 227
V. Enchev G. Ivanova A. Ugrinov G. D. Neykov Tautomeric and conformational equilibrium of acenaphthenequinonemonooxime J. Mol. Struct. 1999 508 149
A. Kržan D. R. Crist V. Horák An ab initio molecular orbital study of nitrosophenol/quinone monooxime equilibria J. Mol. Struct.: THEOCHEM 2000 528 237
G. Ivanova V. Enchev Does tautomeric equilibrium exist in ortho-nitrosonaphthols? Chem. Phys. 2001 264 235
J. A. Long N. J. Harris K. Lammertsma Formaldehyde oxime ⇌ nitrosomethane tautomerism J. Org. Chem. 2001 66 6762
V. Enchev G. Ivanova N. Stoyanov Tautomeric and conformational equilibrium of 2-nitrosophenol and 9,10-phenanthrenequinonemonooxime: Ab initio and NMR study J. Mol. Struct.: THEOCHEM 2003 640 149
E. D. Raczyńska T. M. Krygowski J. E. Zachara B. Ośmiałowski R. Gawinecki Tautomeric equilibria, H-bonding and π-electron delocalization in o-nitrosophenol. A B3LYP/6-311+G(2df,2p) study J. Phys. Org. Chem. 2005 18 892
A. E. Shchavlev A. N. Pankratov V. Enchev Intramolecular hydrogen-bonding interactions in 2-nitrosophenol and nitrosonaphthols: Ab initio, density functional, and nuclear magnetic resonance theoretical study J. Phys. Chem. A 2007 111 7112
V. Enchev S. Angelova Does tautomeric equilibrium exist in 4-nitroso-5-pyrazolones? J. Mol. Struct.: THEOCHEM 2009 897 55
M. Rakhshanipour H. Jalali V. Darugar H. Eshghi M. Vakili Synthesis, structure, tautomerism, intramolecular hydrogen bond, and vibrational assignment of 3-nitroso-2,4-pentanedione: A theoretical and experimental approach Vib. Spectrosc. 2020 107 103036
S. Poorhaji M. Pordel S. Ramezani New heterocyclic green, blue and orange dyes from indazole: Synthesis, tautomerism, alkylation studies, spectroscopic characterization and DFT/TD-DFT calculations J. Mol. Struct. 2016 1119 151
E. D. Ilieva G. P. Petrova R. D. Nikolova G. N. Vayssilov Computational elucidation of the reaction mechanism for synthesis of pyrrolidinedione derivatives: Via Nef-Type rearrangement-cyclization reaction RSC Adv. 2018 8 3178
M. Zhao W. He L. H. Zou D. Wang T. Y. Sun X. F. Xia Iron-catalyzed hydrogen atom transfer induced cyclization of 1,6-enynes for the synthesis of ketoximes: A combined experimental and computational study Org. Chem. Front. 2021 8 643
J. Park I. V. Dyakov A. M. Mebel M. C. Lin Experimental and theoretical studies of the unimolecular decomposition of nitrosobenzene: High-pressure rate constants and the C-N bond strength J. Phys. Chem. A 1997 101 6043
Y. Fu Y. Mou B. L. Lin L. Liu Q. X. Guo Structures of the X-Y-NO Molecules and Homolytic Dissociation Energies of the Y-NO Bonds (Y) C, N, O, (S) J. Phys. Chem. A 2002 106 12386
X. Li H. Deng X. Q. Zhu X. Wang H. Liang J. P. Cheng Establishment of the C-NO bond dissociation energy scale in solution and its application in analyzing the trend of NO transfer from C-nitroso compound to thiols J. Org. Chem. 2009 74 4472
H. Chakrapani M. D. Bartberger E. J. Toone C-nitroso donors of nitric oxide J. Org. Chem. 2009 74 1450
J. C. M. Monbaliu L. K. Beagle J. Kovacs M. Zeller C. V. Stevens A. R. Katritzky En route towards α-benzotriazoyl nitroso derivatives RSC Adv. 2012 2 8941
B. S. Jursic Z. Zdravkovski Theoretical Study of the BH3-Catalyzed Hetero Diels-Alder Reaction between Ethylene and Nitrosoethylene J. Org. Chem. 1995 60 3163
D. Sperling A. Mehlhorn H. U. Reißig J. Fabian Theoretical study of pericyclic reactions of nitrosoethylene and (thionitroso)ethylene Liebigs Ann. 1996 1615
J. Liu S. Niwayama Y. You K. N. Houk Theoretical Prediction and Experimental Tests of Conformational Switches in Transition States of Diels-Alder and 1,3-Dipolar Cycloadditions to Enol Ethers J. Org. Chem. 1998 63 1064
A. G. Leach K. N. Houk Transition states and mechanisms of the hetero-Diels-Alder reactions of hyponitrous acid, nitrosoalkanes, nitrosoarenes, and nitrosocarbonyl compounds J. Org. Chem. 2001 66 5192
M. A. McCarrick Y. D. Wu K. N. Houk Exo-Lone-Pair Effect on Hetero-Diels-Alder Cycloaddition Stereochemistry J. Am. Chem. Soc. 1992 114 1499
M. A. McCarrick Y. D. Wu K. N. Houk Hetero-Diels-Alder Reaction Transition Structures: Reactivity, Stereoselectivity, Catalysis, Solvent Effects, and the exo-Lone-Pair Effect J. Org. Chem. 1993 58 3330
A. G. Leach K. N. Houk Diels-Alder and ene reactions of singlet oxygen, nitroso compounds and triazolinediones: Transition states and mechanisms from contemporary theory Chem. Commun. 2002 1243
Z. X. Yu Y. D. Wu A theoretical study of the mechanisms and regiochemistry of the reactions of 5-alkoxyoxazole with thioaldehydes, nitroso compounds, and aldehydes J. Org. Chem. 2003 68 412
L. R. Domingo M. T. Picher P. Arroyo Towards an understanding of the polar Diels-Alder reactions of nitrosoalkenes with enamines: A theoretical study Eur. J. Org. Chem. 2006 2570
T. C. Wabnitz S. Saaby K. A. Jørgensen The first catalytic inverse-electron demand hetero-Diels-Alder reaction of nitroso alkenes using pyrrolidine as an organocatalyst Org. Biomol. Chem. 2004 2 828
L. R. Domingo P. Pérez J. A. Sáez Understanding the regioselectivity in hetero Diels-Alder reactions. An ELF analysis of the reaction between nitrosoethylene and 1-vinylpyrrolidine Tetrahedron 2013 69 107
J. C. Monbaliu J. Marchand-Brynaert D. Peeters Is anthracene cofactor or spectator for the thermolysis of anthracenyl acylnitroso cycloadducts in the presence of a diene? Tetrahedron Lett. 2009 50 2555
C. K. Jana S. Grimme A. Studer Enantioselective nitroso-Diels-Alder reaction and its application for the synthesis of (-)-peracetylated conduramine A-I Chem.-Eur. J. 2009 15 9078
J. C. Monbaliu B. Tinant D. Peeters J. Marchand-Brynaert Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels-Alder cycloadditions with nitroso and azodicarboxylate dienophiles Tetrahedron Lett. 2010 51 1052
J. C. Monbaliu G. Dive J. Marchand-Brynaert D. Peeters HDA cycloadditions of 1-diethoxyphosphonyl-1,3-butadiene with nitroso heterodienophiles: A computational investigation J. Mol. Struct.: THEOCHEM 2010 959 49
J. M. De Los Santos R. Ignacio G. Rubiales D. Aparicio F. Palacios Hetero-Diels-Alder reaction of phosphinyl and phosphonyl nitroso alkenes with conjugated dienes: An aza-Cope rearrangement J. Org. Chem. 2011 76 6715
J. M. De Los Santos G. Rubiales Z. E. Sbai A. M. Ochoa de Retana F. Palacios Reaction of phosphinylated nitrosoalkenes with electron-rich heterocycles. Electrophilic aromatic substitution vs. cycloaddition Org. Biomol. Chem. 2017 15 662
A. Anand G. Bhargava P. Singh S. Mehra V. Kumar M. P. Mahajan P. Singh K. Bisetty Regio-and Diastereoselective Nitroso Diels-Alder Cycloaddition Reactions of 3-dienyl-2-azetidinones with Nitrosoarenes Lett. Org. Chem. 2012 9 411
L. Cleary V. W. Mak S. D. Rychnovsky K. J. Shea N. Sizemore Origins of regio-and stereochemistry in type 2 intramolecular N-acylnitroso diels-alder reactions: A computational study of tether length and substituent effects J. Org. Chem. 2013 78 4090
J. Pous T. Courant G. Bernadat B. I. Iorga F. Blanchard G. Masson Regio-, Diastereo-, and Enantioselective Nitroso-Diels-Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral Phosphoric Acids J. Am. Chem. Soc. 2015 137 11950
D. Chaiyaveij A. S. Batsanov M. A. Fox T. B. Marder A. Whiting An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4+2] Cycloadditions J. Org. Chem. 2015 80 9518
S. C. C. Nunes S. M. M. Lopes C. S. B. Gomes A. A. C. C. Pais T. M. V. D. Pinho e Melo Reactions of Nitrosoalkenes with Dipyrromethanes and Pyrroles: Insight into the Mechanistic Pathway Sandra J. Org. Chem. 2014 79 10456
S. M. M. Lopes S. C. C. Nunes C. C. Caratão A. A. C. C. Pais T. M. V. D. Pinho e Melo Reactivity of 1-arylnitrosoethylenes towards indole derivatives Monatsh. Chem. 2016 147 1565
W. Ji C. L. Li H. Chen Z. X. Yu X. Liao A newly designed heterodiene and its application to construct six-membered heterocycles containing an N-O bond Chem. Commun. 2019 55 12012
G. Mlostoń K. Urbaniak M. Jasiński E. U. Würthwein H. Heimgartner R. Zimmer H. U. Reissig The [4+2]-Cycloaddition of α-Nitrosoalkenes with Thiochalcones as a Prototype of Periselective Hetero-Diels-Alder Reactions - mdash;Experimental and Computational Studies Chem.-Eur. J. 2020 26 237
Y. Miura H. Ouchi M. Inai T. Osawa F. Yoshimura J. Kanazawa M. Uchiyama M. Kondo T. Kan Synthetic Studies on Pactamycin: A Synthesis of Johnson's Intermediate Org. Lett. 2020 22 3515
P. A. Nocquet S. Henrion A. Macé B. Carboni J. M. Villalgordo F. Carreaux The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C-N Bonds Eur. J. Org. Chem. 2017 1295
W. Adam N. Bottke B. Engels O. Krebs An experimental and computational study on the reactivity and regioselectivity for the nitrosoarene ene reaction: Comparison with triazolinedione and singlet oxygen J. Am. Chem. Soc. 2001 123 5542
A. G. Leach K. N. Houk The ene reactions of nitroso compounds involve polarized diradical intermediates J. Am. Chem. Soc. 2002 124 14820
X. Lu Can the nitroso ene reaction proceed concertedly? Org. Lett. 2004 6 2813
P. Quadrelli M. Mella A. Piccanello S. Romano P. Caramella Variable Markovnikov orientation and "cis effect" in ene reactions of nitrosocarbonyl intermediates J. Org. Chem. 2007 72 1807
L. Zhai X. Tian C. Wang Q. Cui W. Li S. H. Huang Z. X. Yu R. Hong Construction of Morphan Derivatives by Nitroso-Ene Cyclization: Mechanistic Insight and Total Synthesis of (±)-Kopsone Angew. Chem., Int. Ed. 2017 56 11599
T. Sasaki Y. Ishibashi M. Ohno Unequivocal Synthesis Of Phenacylideneaniline From Silyl Enol Ethers And Nitrosobenzene And One-Pot Cycloaddition Reactions Of The Related Anils Chem. Lett. 1983 12 863
T. Sasaki K. Mori M. Ohno Synthesis of β-N-Phenylamino Alcohols and α-N-Phenylamino Acids via Reduction of the Adducts of Silyl Enol Ethers and Bis-silyl Ketene Acetals with Nitrosobenzene Synthesis 1985 280
P. H. Y. Cheong K. N. Houk Origins of selectivities in proline-catalyzed α-aminoxylations J. Am. Chem. Soc. 2004 126 13912
A. Córdova H. Sundén A. Bøgevig M. Johansson F. Himo The direct catalytic asymmetric α-aminooxylation reaction: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations Chem.-Eur. J. 2004 10 3673
H. Wang C. Yang K. Han Density functional study of the L-proline-catalyzed α-aminoxylation of aldehydes reaction: The reaction mechanism and selectivity Struct. Chem. 2006 17 97
J. Joseph D. B. Ramachary E. D. Jemmis Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis Org. Biomol. Chem. 2006 4 2685
R. Zhu D. Zhang J. Wu C. Liu A DFT study on the mechanism and regioselectivity of the tandem O-nitroso aldol/Michael reaction of nitrosobenzene and cyclohexanone J. Mol. Struct.: THEOCHEM 2007 815 105
M. Akakura M. Kawasaki H. Yamamoto DFT study of brønsted acid catalyzed nitroso aldol reaction between achiral enamines and nitrosobenzene: The reason for regio-and enantioselectivity Eur. J. Org. Chem. 2008 4245
M. Lu Y. Lu D. Zhu X. Zeng X. Li G. Zhong Chiral brønsted acid catalyzed enantioselective α-aminoxylation of enecarbamates Angew. Chem., Int. Ed. 2010 49 8588
C. T. Wong A theoretical investigation on the mechanism of the α,α-diphenylprolinol trimethylsilyl ether-catalyzed oxyamination reaction Tetrahedron Lett. 2009 50 811
A. Mielgo I. Velilla E. Gómez-Bengoa C. Palomo Brønsted acid assisted regio-and enantioselective direct o-nitroso aldol reaction catalysed by α,α-diphenylprolinol trimethylsilyl ether Chem.-Eur. J. 2010 16 7496
C. Palomo S. Vera I. Velilla A. Mielgo E. Gómez-Bengoa Regio-and Enantioselective Direct Oxyamination Reaction of Aldehydes Catalyzed by α,α-Diphenylprolinol Trimethylsilyl Ether Angew. Chem. 2007 119 8200
L. Zhang C. Xu X. Mi S. Luo Origins of the enantio-and N/O selectivity in the primary-amine-catalyzed hydroxyamination of 1,3-dicarbonyl compounds with in situ-formed nitrosocarbonyl compounds: A theoretical study Chem.-Asian J. 2014 9 3565
D. J. Nelson R. Kumar Shagufta Regiochemical reversals in nitrosobenzene reactions with carbonyl compounds-α-aminooxy ketone versus α-hydroxyamino ketone products Eur. J. Org. Chem. 2012 6013
C. Volpe S. Meninno A. Roselli M. Mancinelli A. Mazzanti A. Lattanzi Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study Adv. Synth. Catal. 2020 362 5457
S. Ham D. M. Bimey An ab fnitio Study of the Reactivity of Nitrosoketene with Formaldehyde Tetrahedron Lett. 1994 35 8113
S. Ham D. M. Birney Further Ab initio studies on the reactivity of nitrosoketene Tetrahedron Lett. 1997 38 5925
H. Tanimoto T. Shitaoka K. Yokoyama T. Morimoto Y. Nishiyama K. Kakiuchi Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones J. Org. Chem. 2016 81 8722
A. Jabbari K. N. Houk Hetero-Cope rearrangements of nitrosobutenes. DFT studies of thermal and acid-catalyzed reactions Org. Lett. 2006 8 5975
A. Penoni G. Palmisano Y. L. Zhao K. N. Houk J. Volkman K. M. Nicholas On the Mechanism of Nitrosoarene-Alkyne Cycloaddition J. Am. Chem. Soc. 2009 131 653
I. Chatterjee C. K. Jana M. Steinmetz S. Grimme A. Studer Copper-catalyzed enantioselective [2.+2] cycloadditions of 2-nitrosopyridine with ketenes Adv. Synth. Catal. 2010 352 945
F. Weigend A fully direct RI-HF algorithm: Implementation, optimised auxiliary basis sets, demonstration of accuracy and efficiency Phys. Chem. Chem. Phys. 2002 4 4285
R. S. Srivastava N. R. Tarver K. M. Nicholas Mechanistic studies of copper(i)-catalyzed allylic amination J. Am. Chem. Soc. 2007 129 15250
O. A. Levitskiy Y. K. Grishin V. V. Sentyurin T. V. Magdesieva Copper-Assisted Amination of Boronic Acids for Synthesis of Bulky Diarylamines: Experimental and DFT Study Chem.-Eur. J. 2017 23 12575
A. Pokluda M. Kohout J. Chudoba M. Krupička R. Cibulka Nitrosobenzene: Reagent for the Mitsunobu Esterification Reaction ACS Omega 2019 4 5012
M. Castiñeira Reis M. Marín-Luna C. Silva López O. N. Faza Mechanism of the Molybdenum-Mediated Cadogan Reaction ACS Omega 2018 3 7019