Role of substituents on resonance assisted hydrogen bonding: Vs. intermolecular hydrogen bonding

The role of substituents on resonance assisted hydrogen bonding (RAHB) vs. intermolecular hydrogen bonding is highlighted in known arylhydrazones of active methylene compounds (AHAMCs) and in their new representatives-(E/Z)-2-(2-(para-substitutedphenyl)hydrazineylidene)-N,N-diethyl-3-oxobutanamides (-C2H5,-H,-COOH,-CN). The strength of the H-bond depends on the attached functional groups to both the active methylene fragment and the aromatic moiety of the AHAMC. For instance, attachment of the strong electron donor group-N(C2H5)2 (σp =-0.72) to the active methylene fragment of AHAMC allows to isolate this class of compounds without RAHB but with strong intermolecular H-bonds, which are the first examples reported herein. © 2020 The Royal Society of Chemistry.

Авторы
Gurbanov A.V. 1, 2 , Kuznetsov M.L.1 , Demukhamedova S.D.3 , Alieva I.N.3 , Godjaev N.M.3 , Zubkov F.I. 4 , Mahmudov K.T. 1, 2 , Pombeiro A.J.L. 1
Журнал
Издательство
Royal Society of Chemistry
Номер выпуска
4
Язык
Английский
Страницы
628-633
Статус
Опубликовано
Том
22
Год
2020
Организации
  • 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisboa, 1049-001, Portugal
  • 2 Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
  • 3 Institute for Physical Problems, Baku State University, Z. Xalilov Str. 23, Baku, Az 1148, Azerbaijan
  • 4 Organic Chemistry Department, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Ключевые слова
Hydrogen; Active methylene compounds; Aromatic moieties; Electron donors; H-bonds; Intermolecular hydrogen bonding; Hydrogen bonds
Дата создания
10.02.2020
Дата изменения
10.02.2020
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/56594/