Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones

N. N. Chipanina; L. P. Oznobikhina; M. V. Sigalov; V. Yu Serykh; B. A. Shainyan

doi:10.1134/S1070363221060050

Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones

N. N. Chipanina, L. P. Oznobikhina, M. V. Sigalov, V. Yu Serykh, B. A. Shainyan

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Abstract: To assess the donor-acceptor properties of the basic and acidic sites inpyrrolyl and diazolyl derivatives of cycloalkanones, the energies and the shapesof the frontier molecular orbitals of their tautomers and conformers werecalculated and the maps of the charge density distribution were constructed. Thecompetition of these sites in the formation of hydrogen and coordination bondsand the possibility of participation of the studied products as ligands in metalcomplexes were shown. Complexes of diazolyl derivatives withCuCl₂ were obtained. The synthesis of7-amino-2-(pyrrolidin-2-ylmethylene)indan-1-one was performed and its structureand propensity to UV-initiated E→Z isomerization were studied by NMR and IRspectroscopy. [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	991-1008
Number of pages	18
Journal	Russian Journal of General Chemistry
Volume	91
Issue number	6
DOIs	https://doi.org/10.1134/S1070363221060050
State	Published - 1 Jun 2021

Keywords

NMR and IR spectroscopy
charge density distribution
copper(II) complexes
cycloalkanones pyrrolyl (diazolyl) derivatives
theoretical calculations

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1134/S1070363221060050

Cite this

@article{fb2d5cdc60664bdea6db5b6efb6e3c02,

title = "Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones",

abstract = "Abstract: To assess the donor-acceptor properties of the basic and acidic sites inpyrrolyl and diazolyl derivatives of cycloalkanones, the energies and the shapesof the frontier molecular orbitals of their tautomers and conformers werecalculated and the maps of the charge density distribution were constructed. Thecompetition of these sites in the formation of hydrogen and coordination bondsand the possibility of participation of the studied products as ligands in metalcomplexes were shown. Complexes of diazolyl derivatives withCuCl2 were obtained. The synthesis of7-amino-2-(pyrrolidin-2-ylmethylene)indan-1-one was performed and its structureand propensity to UV-initiated E→Z isomerization were studied by NMR and IRspectroscopy. [Figure not available: see fulltext.]",

keywords = "NMR and IR spectroscopy, charge density distribution, copper(II) complexes, cycloalkanones pyrrolyl (diazolyl) derivatives, theoretical calculations",

author = "Chipanina, {N. N.} and Oznobikhina, {L. P.} and Sigalov, {M. V.} and Serykh, {V. Yu} and Shainyan, {B. A.}",

note = "Publisher Copyright: {\textcopyright} 2021, Pleiades Publishing, Ltd.",

year = "2021",

month = jun,

day = "1",

doi = "10.1134/S1070363221060050",

language = "English",

volume = "91",

pages = "991--1008",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "Pleiades Publishing",

number = "6",

}

TY - JOUR

T1 - Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones

AU - Chipanina, N. N.

AU - Oznobikhina, L. P.

AU - Sigalov, M. V.

AU - Serykh, V. Yu

AU - Shainyan, B. A.

PY - 2021/6/1

Y1 - 2021/6/1

N2 - Abstract: To assess the donor-acceptor properties of the basic and acidic sites inpyrrolyl and diazolyl derivatives of cycloalkanones, the energies and the shapesof the frontier molecular orbitals of their tautomers and conformers werecalculated and the maps of the charge density distribution were constructed. Thecompetition of these sites in the formation of hydrogen and coordination bondsand the possibility of participation of the studied products as ligands in metalcomplexes were shown. Complexes of diazolyl derivatives withCuCl2 were obtained. The synthesis of7-amino-2-(pyrrolidin-2-ylmethylene)indan-1-one was performed and its structureand propensity to UV-initiated E→Z isomerization were studied by NMR and IRspectroscopy. [Figure not available: see fulltext.]

AB - Abstract: To assess the donor-acceptor properties of the basic and acidic sites inpyrrolyl and diazolyl derivatives of cycloalkanones, the energies and the shapesof the frontier molecular orbitals of their tautomers and conformers werecalculated and the maps of the charge density distribution were constructed. Thecompetition of these sites in the formation of hydrogen and coordination bondsand the possibility of participation of the studied products as ligands in metalcomplexes were shown. Complexes of diazolyl derivatives withCuCl2 were obtained. The synthesis of7-amino-2-(pyrrolidin-2-ylmethylene)indan-1-one was performed and its structureand propensity to UV-initiated E→Z isomerization were studied by NMR and IRspectroscopy. [Figure not available: see fulltext.]

KW - NMR and IR spectroscopy

KW - charge density distribution

KW - copper(II) complexes

KW - cycloalkanones pyrrolyl (diazolyl) derivatives

KW - theoretical calculations

UR - http://www.scopus.com/inward/record.url?scp=85111678676&partnerID=8YFLogxK

U2 - 10.1134/S1070363221060050

DO - 10.1134/S1070363221060050

M3 - Article

AN - SCOPUS:85111678676

SN - 1070-3632

VL - 91

SP - 991

EP - 1008

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

IS - 6

ER -

Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this