Theoretical determination of molecular structure and conformation. Part 12. Puckering of 1,3,5-cycloheptatriene, 1H-azepine, oxepine and their norcaradienic valence tautomers

URN to cite this document:

urn:nbn:de:bvb:355-epub-54939 Copy

DOI to cite this document:

10.5283/epub.5493 Copy

Cremer, Dieter ; Dick, Bernhard ; Christeu, Dines

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Date of publication of this fulltext: 05 Aug 2009 13:50

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Item type:	Article
Journal or Publication Title:	Theochem. Journal of Molecular Structure
Publisher:	Elsevier
Volume:	19
Number of Issue or Book Chapter:	3-4
Page Range:	pp. 277-291
Date:	1984
Additional Information (public):	CAN 102:94944 22-2 Physical Organic Chemistry 291-70-3; 544-25-2; 1488-25-1; 12764-48-6; 14515-09-4; 57784-62-0 Role: PRP (Properties) (geometry and conformation of)
Institutions:	Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry III - Physical Chemistry (Molecular Spectroscopy and Photochemistry) > Prof. Dr. Bernhard Dick
Identification Number:	Value Type 1985:94944 Other 10.1016/0166-1280(84)80077-9 DOI
Keywords:	Transition state structure (conformation inversion in cyclohexatriene, azepine, oxepin and their norcaradienic valence tautomers); Inertia (moment of, with cyclohexatrienes); Molecular orbital (of cycloheptatriene, azepine, oxepin and their norcaradienic valence tautomers); Conformation and Conformers; Molecular structure (of cycloheptatriene, azepine, oxepin, and their norcaradienic valence tautomers); Potential barrier (inversional, of cycloheptatriene, azepine, oxepin, and their norcaradienic valence tautomers); MO cycloheptatriene azepine oxepin; geometry cycloheptatriene azepine oxepin; conformation cycloheptatriene azepine oxepin; inversion barrier cycloheptatriene azepine oxepin
Dewey Decimal Classification:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	No
Item ID:	5493

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Abstract

RHF calcns. have been carried out for 1,3,5-cycloheptatriene, norcaradiene, 1H-azepine, benzenimine (azanorcaradiene), oxepin and benzene oxide (oxanorcaradiene) employing the STO-3G, 4-31G and 6-31G* basis sets. Theor. geometries, conformation and barriers to ring inversion have been obtained and compared with the available exptl. structural data. The cyclotrienes possess a boat conformation ...

Abstract

RHF calcns. have been carried out for 1,3,5-cycloheptatriene, norcaradiene, 1H-azepine, benzenimine (azanorcaradiene), oxepin and benzene oxide (oxanorcaradiene) employing the STO-3G, 4-31G and 6-31G* basis sets. Theor. geometries, conformation and barriers to ring inversion have been obtained and compared with the available exptl. structural data. The cyclotrienes possess a boat conformation with a const. admix. of 22% chair character leading to a flattening of the triene part and p-electron delocalization typical for a planar polyene. The structural data suggest that cyclic delocalization of either 6p (homoaromaticity) or 8p electrons (antiaromaticity) is not present in the 3 cyclotrienes. The former possibility, however, cannot be excluded in the case of 3 norcaradienes.

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