Work

Effect of substituent position on assembly of compounds bearing ortho/para over meta directing groups

Year: 2024

Type: article

Abstract: This research investigated the impact of substituent location on intermolecular interactions and crystal packing. A class of N -(dichlorophenyl)-2-pyrazincarboxamide derivatives were synthesized and characterized: 2,5-dichloro ( 2,5-diCl ), 3,4-dichloro ( 3,4-diCl ), and 2,4-dichloro ( 2,4-diCl ). Comparison with their monochloro counterparts (2-chloro ( 2-Cl ), 3-chloro ( 3-Cl ), and 4-chloro ( 4-Cl )) revealed a distinct structural variation upon introducing a second chlorine substituent at the ortho / para positions of the phenyl ring. Conversely, incorporating a second chlorine atom at the meta position resulted in similar molecular packing. These findings suggest that ortho / para directing groups play a dominant role in dictating the crystal assemblies of the studied compounds.

Source: Results in Chemistry

DOI: 10.1016/j.rechem.2024.101748

Authors: Vahid Amani, Fataneh Norouzi, Maryam Esmaeili, Hamid Reza Khavasi

Institutions: Farhangian University, Shahid Beheshti University

Language: English

Topic: Crystallography and molecular interactions

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,490

Funder: Farhangian University