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.

Authors
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
Journal
Publisher
Royal Society of Chemistry
Number of issue
4
Language
English
Pages
628-633
Status
Published
Volume
22
Year
2020
Organizations
  • 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
Keywords
Hydrogen; Active methylene compounds; Aromatic moieties; Electron donors; H-bonds; Intermolecular hydrogen bonding; Hydrogen bonds
Date of creation
10.02.2020
Date of change
10.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/56594/
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