Intramolecular hydrogen bonds in 1,4-dihydropyridine derivatives

被引：15

作者：

Petrova, M. ^{[1
]}

Muhamadejev, R. ^{[1
]}

Vigante, B. ^{[1
]}

Duburs, G. ^{[1
]}

Liepinsh, Edvards ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, Aizkraukles 21 St, LV-1006 Riga, Latvia

来源：

ROYAL SOCIETY OPEN SCIENCE | 2018年 / 5卷 / 06期

关键词：

NMR; DFT; 1; 4-dihydropyridines; hydrogen bond; H/D C-13 isotope effects; IR; CHEMICAL-SHIFTS; NMR; DEPENDENCE; ENERGIES;

D O I：

10.1098/rsos.180088

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

1,4-Dihydropyridine (1,4-DHP) derivatives have been synthesized and characterized by H-1,C- 13, N-15 nuclear magnetic resonance (NMR) spectroscopy, secondary proton/deuterium C-13 isotope shifts, variable temperature H-1 NMR experiments and quantum-chemical calculation. The intramolecular hydrogen bonds NH center dot center dot center dot O=C and CH center dot center dot center dot O=C in these compounds were established by NMR and quantumchemical studies The downfield shift of the NH proton, accompanied by the upfield shift of the N-15 nuclear magnetic resonance signals, the shift to the higher wavenumbers of the NH stretching vibration in the infrared spectra and the increase of the (1)J(N-15,(1)<^>H) values may indicate the shortening of the N-H bond length upon intramolecular N center dot center dot center dot O0=C hydrogen bond formation.

引用

页数：15

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