Modelling biologically important NH•••π interactions

doi:10.1070/RCR5047

2022-07-01

PRE

А. Ф. Пожарский *

Olga V. Dyablo

Valery A. Ozeryanskii

Olga G. Pogosova

DOI：10.1070/RCR5047

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摘要

En 中文

The review summarizes the information accumulated to date on NH center dot center dot center dot pi interactions, which represent an unconventional type of hydrogen bonding between the NH-donor (most often amines, carboxamides or NH heterocycles) and a proton acceptor (usually an electron-rich aromatic or heteroaromatic rings). The importance of NH center dot center dot center dot pi interactions stems mainly from their involvement in the structuring of proteins and some other biomolecules, as well as in molecular recognition processes. The growth of knowledge on NH center dot center dot center dot pi interactions contributes to a better understanding of complex biochemical processes, stimulates the development of new drugs and improved methods of their targeted delivery. Since the study of NH center dot center dot center dot pi interactions on living tissues is rather difficult, their modelling on various synthetic objects has become widespread. In the review, various types of such models are systematized and compared in regard of their geometry, stereo dynamics, and NH center dot center dot center dot pi binding energy. Examples of reactions driven by NH center dot center dot center dot pi interaction are given, as well as examples of practical use. A rational classification of existing models is proposed, which facilitates their convenient consideration.

Keyword:

HYDROGEN-BONDED COMPLEXES

MOLECULAR-STRUCTURE

CRYSTAL-STRUCTURE

SOLID-STATE

CATION-PI

X-RAY

STRUCTURAL-CHARACTERIZATION

INTERMOLECULAR INTERACTIONS

AMMONIUM TETRAPHENYLBORATE

VIBRATIONAL SPECTROSCOPY