Electron conjugation versus π–π repulsion in substituted benzenes: why the carbon–nitrogen bond in nitrobenzene is longer than in aniline-Reference-Cited by-同舟云学术

Electron conjugation versus π–π repulsion in substituted benzenes: why the carbon–nitrogen bond in nitrobenzene is longer than in aniline

Published:2016 Issue:17 Volume:18 Page:11821-11828
ISSN:1463-9076
Container-title:Physical Chemistry Chemical Physics
language:en
Short-container-title:Phys. Chem. Chem. Phys.

Author:

Zhang Huaiyu¹²³⁴⁵,Jiang Xiaoyu⁶⁷⁸⁹,Wu Wei¹²³⁴⁵,Mo Yirong¹⁰¹¹¹²¹³

Affiliation:

1. The State Key Laboratory of Physical Chemistry of Solid Surfaces

2. iChEM

3. Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry and College of Chemistry and Chemical Engineering

4. Xiamen University

5. Xiamen

6. College of Ecological Environment and Urban Construction

7. Fujian University of Technology

8. Fuzhou 350108

9. China

10. Department of Chemistry

11. Western Michigan University

12. Kalamazoo

13. USA

Abstract

Computations show that the enhanced π–π repulsion in nitrobenzene, contributed by both the electrostatic interaction and the Pauli exchange, is responsible for the stretched C–N bond in nitrobenzene (1.486 Å) compared with the C–N bond in aniline (1.407 Å).

Funder

Directorate for Computer and Information Science and Engineering

Division of Chemistry

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Link

http://pubs.rsc.org/en/content/articlepdf/2016/CP/C6CP00471G

Reference98 articles.

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2. G. W. Wheland , The Theory of Resonance, John Wiley & Sons, New York, 1944