Substituent effects of nitro group in cyclic compounds
Authors:
- Anna Jezuita,
- K. Ejsmont,
- Halina Szatyłowicz
Abstract
Numerous studies on nitro group properties are associated with its high electron-withdrawing ability, by means of both resonance and inductive effect. The substituent effect of the nitro group may be well described using either traditional substituent constants or characteristics based on quantum chemistry, i.e., cSAR, SESE, and pEDA/sEDA models. Interestingly, the cSAR descriptor allows to describe the electron-attracting properties of the nitro group regardless of the position and the type of system. Analysis of classical and reverse substituent effects of the nitro group in various systems indicates strong pi-electron interactions with electron-donating substituents due to the resonance effect. This significantly affects the pi-electron delocalization of the aromatic ring decreasing the aromatic character, evidenced clearly by HOMA values. Use of the pEDA/sEDA model allows to measure the population of electrons transferred from the ring to the nitro group.
- Record ID
- WUT10f11a118ea549718a4ec9e9204144ca
- Author
- Journal series
- Structural Chemistry, ISSN 1040-0400, e-ISSN 1572-9001
- Issue year
- 2021
- Vol
- 32
- Pages
- 179-203
- Publication size in sheets
- 1.20
- Keywords in English
- Nitrogroup, Substituent effects, Molecularmodeling, Sigma and pi electronstructure, Substituent effect stabilization energy, Charge of the substituent active region
- ASJC Classification
- ;
- DOI
- DOI:10.1007/s11224-020-01612-x Opening in a new tab
- URL
- https://link.springer.com/article/10.1007/s11224-020-01612-x Opening in a new tab
- Language
- (en) English
- File
-
- File: 1
- wdpb_publikacje_pliki_plik_publikacja_4152_org.pdf
-
- Score (nominal)
- 70
- Score source
- journalList
- Score
- = 70.0, 24-05-2022, ArticleFromJournal
- Publication indicators
- = 7; : 2017 = 0.525; : 2020 (2 years) = 1.887 - 2020 (5 years) =1.494
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- Uniform Resource Identifier
- https://repo.pw.edu.pl/info/article/WUT10f11a118ea549718a4ec9e9204144ca/
- URN
urn:pw-repo:WUT10f11a118ea549718a4ec9e9204144ca
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.