Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a "through space" amide

被引：7

作者：

Wannebroucq, Amelie ^{[1
]}

Jarmyn, Andrew P. ^{[1
]}

Pitak, Mateusz B. ^{[2
]}

Coles, Simon J. ^{[2
]}

Wallis, John D. ^{[1
]}

机构：

[1] Nottingham Trent Univ, Sch Sci & Technol, Clifton Lane, Nottingham NG11 8NS, England

[2] Univ Southampton, UK Natl Crystallog Serv, Highfield Campus, Southampton SO17 1BJ, Hants, England

来源：

PURE AND APPLIED CHEMISTRY | 2016年 / 88卷 / 04期

关键词：

acylation; aldehydes; ESOC-19; hydrogen bonding; intramolecular reactivity; NAPHTHALENES; PROTONATION; BOND;

D O I：

10.1515/pac-2015-1103

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

8-Dimethylaminonaphthalene-1-carbaldehyde reacts readily at 0 degrees C with benzoyl or pivaloyl chloride by O-acylation and formation of a N-C bond (1.566(2)-1.568(3) angstrom) between the peri-substituents to give a salt. The reaction is promoted by electron donation from the dimethylamino group to the carbonyl group, akin to the properties of an amide. In contrast, the corresponding methyl ester and N,N-diisopropylamide react with acid in ether by protonation of the dimethylamino group and formation of a hydrogen bond to the carbonyl group, while under similar conditions the N,N-dimethylamide undergoes ready hydrolysis to the acid. The structures of products are determined by X-ray crystallography, and from the latter hydrolysis crystals containing zwitterionic 1-dimethylammonium-naphthalene-8-carboxylate and the corresponding O-protonated cation along with dimethylammonium and triflate ions were obtained.

引用

页码：317 / 331

页数：15