The electronic structure of β-propiolactone (2-oxetanone) and of some 3- and 4-substituted 2-oxetanones

[en] STO-3G calculations were performed on several 4-substituted 2-oxetanones (β-lactones), with the aim of rationalizing their very different chemical stabilities. A direct correlation was found between the relative thermal stabilities of the substituted β-lactones and the respective energies of their HOMO and LUMO. © 1984.

Disciplines :

Chemistry

Author, co-author :

Noels, Alfred ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Herman, J. J.; Laboratoire de Chimie Macromoléculaire et de Catalyse Organique, Université de Liège, Sart-Tilman, B-4000 Liège, Belgium

Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

André, Jean-Marie; Université de Namur - UNamur

Delhalle, J.; Laboratoire de Chimie Théorique Appliquée, Facultés Universitaires Notre-Dame de la Paix, B-5000 Namur, Belgium

Fripiat, J. G.; Laboratoire de Chimie Théorique Appliquée, Facultés Universitaires Notre-Dame de la Paix, B-5000 Namur, Belgium

Language :

English

Title :

The electronic structure of β-propiolactone (2-oxetanone) and of some 3- and 4-substituted 2-oxetanones

Publication date :

1984

Journal title :

Journal of Molecular Structure: Theochem

ISSN :

0166-1280

Publisher :

Elsevier, Netherlands

Volume :

109

Issue :

3-4

Pages :

293-303

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 14 December 2019

Statistics

Number of views

97 (1 by ULiège)

Number of downloads

91 (3 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Chapman (1973) Mercury photosensitized oxidation of primary and secondary aliphatic amines. Journal of the American Chemical Society 95:617.
Chapman J. Am. Chem. Soc. 1973, 95:1337.
Ozaki (1972) Recent Advances in Isocyanate Chemistry. Chemical Reviews 72:479.
Krapcho, Jahngen J. Org. Chem. 1974, 39:1650.
Fujsawa, Sato, Itoh (1982) A novel synthesis of royal jelly acids and queen substance by the five carbon homologation using .BETA.-vinyl-.BETA.-propiolactone. Chemistry Letters 2:219.
Adam, Martinez, Thomson, Yani (1981) .beta.-Lactones as convenient precursors to sterically congested olefins. The Journal of Organic Chemistry 46:3359.
Liao, Lin, Hsen, Tang, Wang (1982) Photochemistry of syn- and anti-9,10-epoxy-1,4-dihydro-1,4-dipropyl-1,4-ethanonaphthalene-2,3-dione. Journal of the American Chemical Society 104:293.
Lundberg, Cox Ring-Opening Polymerization , Marcel Dekker, New York; 1969, 247-297.
Brode, Koleske J. Makromol. Chem. 1972, 6 A:1104.
Brash, Lyman Cyclic Monomers , Wiley Interscience, New York; 1972, 151.
McCain, Marcus J. Org. Chem. 1970, 35:2414.
Olah, Ku J. Org. Chem. 1970, 35:3917.
Hogeveen (1968) Chemistry and spectroscopy in strongly acidic solutions. Part XIX: Behaviour of α,α-dimethyl-β-propiolactone and hydroxypivalic acid in hydrogen fluoride-boron trifluoride solution. Recueil des Travaux Chimiques des Pays-Bas 87:1303.
Noels, Herman, Teyssité J. Org. Chem. 1976, 41:2527.
Hehre, Stewart, Pople J. Chem. Phys. 1969, 51:2657.
Hehre, Ditchfield, Stewart, Pople J. Chem. Phys. 1970, 64:5142.
Pople Modern Theoretical Chemistry , H.F. Schaefer III, Plenum Press, New York; 1977, 4:1-27.
Binkley, Whiteside, Krishanan, Seeger, Defrees, Schbegel, Topiol, Kahn, Pople QCPE 1981, 13:406.
André, André, Leroy (1971) Etude th�orique de quelques cycles � quatre pi�ces. Theoretica Chimica Acta 21:28.
Thomson (1980) Int. J. Quantum Chem. Int. J. Quantum Chem. , QBS7; 163.
Thomson J. Mol. Struct., Theochem 1982, 88:55.
Bregman, Bauer J. Am. Chem. Soc. 1955, 77:1955.
Boone, Britt, Boggs (1965) Microwave Spectrum, Dipole Moment, and Ring-Puckering Vibration of β-Propiolactone. The Journal of Chemical Physics 43:1190.
Martino, Shevlin, Worley Chem. Phys. Lett. 1979, 68:237.