π-Delocalization in the vicinal lone pairs of hydrazines: Electronic effects in derivatives of 1-(2-nitrophenyl)-1-phenylhydrazine
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- 作者：Joë ; l Poisson ; Ian S. Butler ; D. Scott Bohle<sup> ; sup><sup>scott.bohle@mcgill.ca" class="auth_mail" title="E-mail the corresponding authorsup>
- 关键词：Nitrogen chemistry ; Hydrazines ; Stereochemistry
- 刊名：Journal of Molecular Structure
- 出版年：2016
- 出版时间：15 July 2016
- 年：2016
- 卷：1116
- 期：Complete
- 页码：30-36
- 全文大小：974 K
文摘
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There is a marked electronic interplay between the diaryl system and any substituents on the terminal NH<sub>2sub> group.
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These are nearly unaffected by intermolecular interactions as demonstrated by UV–visible data.
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The balance of the electronic environments in these hydrazines can be quantified in the solid-state by measuring the N–N bond lengths.
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This bond length is surprisingly variable and can vary from a long N–N bond typical of hydrazine itself, to a short N=N double bond.
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Our results, supported by DFT calculations, suggest that the π-contribution to the short bond distances is minimal.