NDLI: Molecular structure and relative stability of trans and cis isomers of formanilide: gas-phase electron diffraction and quantum chemical studies

Content Provider	Springer Nature Link
Author	Marochkin, Ilya I. Dorofeeva, Olga V.
Copyright Year	2012
Abstract	Molecular structure of formanilide is determined by gas-phase electron diffraction (GED) augmented by quantum chemical calculations (B3LYP/cc-pVTZ and MP2/cc-pVTZ) and literature microwave (MW) data. The combined GED and MW data are well reproduced for the mixture of trans and cis isomers with the relative abundance of 59 ± 5 and 41 ± 5 %, respectively, at T = 410 K. The trans isomer (C $_{s}$ symmetry) is planar, while the cis isomer (C $_{1}$ symmetry) has the twisted structure with the amide group rotated by 36.7 ± 2.7° with respect to the phenyl ring. In accord with theoretical calculations, the amide bond –NH–C(O)– is planar in trans formanilide and a somewhat nonplanar in cis isomer. Accurate structural parameters were obtained by a simultaneous fit of the rotational constants reported in the literature and GED intensities obtained in this study. The N–C(O) and N–C$_{Ph}$ bond dissociation energies in formanilide are calculated using Gaussian-4 method. It is revealed that the strength of N–C(O) bond in formanilide is 50 kJ/mol less than that in benzamide. On the contrary, the strength of adjacent bond (N–C$_{Ph}$) increases by 35 kJ/mol compared to aniline. It is rather unexpectedly that the bond strength weakening does not result in the bond elongating, and vice versa.
Starting Page	233
Ending Page	242
Page Count	10
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	24
Issue Number	1
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2012-06-09
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Formanilide Molecular structure Isomers Gas-phase electron diffraction Ab initio and DFT calculations Bond energy Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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