Resonance in formamide: Resolution of contending models

Harold Basch; Shmaryahu Hoz

doi:10.1016/s0009-2614(98)00846-x

Resonance in formamide: Resolution of contending models

Harold Basch, Shmaryahu Hoz

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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Abstract

Resonance in formamide has been investigated by carrying out ab initio VBSCF calculations in an extended Gaussian basis set. It is found that the special properties of the planar geometry C-N bond arise from a π space interaction that involves a N→C donation to a highly polarized carbonyl group. The net result is that the double bond structure in planar formamide looks like the classical H₂N⁺=C(H)O^- distribution. In the C-N rotated geometry the corresponding n-σ* interaction is much less stabilizing. The N→C model resolves some of the differences between the classical amide resonance and Wiberg models for formamide.

Original language	English
Pages (from-to)	117-125
Number of pages	9
Journal	Chemical Physics Letters
Volume	294
Issue number	1-3
DOIs	https://doi.org/10.1016/s0009-2614(98)00846-x
State	Published - 11 Sep 1998

Bibliographical note

Funding Information:
The help of Professor Joop van Lenthe and Dr. Pinchas Aped with the TURTLE code is gratefully acknowledged. This work was supported by a grant from the Israel Science Foundation (484/95).

Funding

The help of Professor Joop van Lenthe and Dr. Pinchas Aped with the TURTLE code is gratefully acknowledged. This work was supported by a grant from the Israel Science Foundation (484/95).

Funders	Funder number
Israel Science Foundation	484/95

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title = "Resonance in formamide: Resolution of contending models",

abstract = "Resonance in formamide has been investigated by carrying out ab initio VBSCF calculations in an extended Gaussian basis set. It is found that the special properties of the planar geometry C-N bond arise from a π space interaction that involves a N→C donation to a highly polarized carbonyl group. The net result is that the double bond structure in planar formamide looks like the classical H2N+=C(H)O- distribution. In the C-N rotated geometry the corresponding n-σ* interaction is much less stabilizing. The N→C model resolves some of the differences between the classical amide resonance and Wiberg models for formamide.",

author = "Harold Basch and Shmaryahu Hoz",

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AU - Hoz, Shmaryahu

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Resonance in formamide: Resolution of contending models

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