Halogen bonding synthon crossover in conformational polymorphism

被引：26
作者：
Khavasi, Hamid Reza [1 ]
Tehrani, Alireza Azhdari [1 ]
机构：
[1] Shahid Beheshti Univ, Fac Chem, GC, Tehran 1983963113, Iran
来源：
CRYSTENGCOMM | 2013年 / 15卷 / 29期
关键词：
REGULAR 2-COMPONENT HAMILTONIANS; DENSITY-FUNCTIONAL THEORY; INTERMOLECULAR INTERACTIONS; SUPRAMOLECULAR CHEMISTRY; CONCOMITANT POLYMORPHS; MOLECULAR-STRUCTURES; PI STACKING; AB-INITIO; COORDINATION; HYDROGEN;
D O I：
10.1039/c3ce40600h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two concomitant conformational polymorphs of N-(3-bromophenyl)-2-pyrazinecarboxamide have been discovered and characterized. The synthon crossover between Br center dot center dot center dot Br and Br center dot center dot center dot N "halogen bonding" on the formation of these polymorphs has been investigated by Hirshfeld surface analysis, halogen bonding interaction energy, lattice energy calculations and calorimetric analysis. From our results, it can be seen that different halogen bonding synthons, along with other intermolecular interactions, namely hydrogen bonding and pi-pi stacking interactions, result in the formation of different conformational polymorphs.
引用
收藏
页码：5813 / 5820
页数：8
相关论文
共 77 条
[41]   Polymorphism in homochiral zinc phosphonates [J].
Liu, Xun-Gao ;
Bao, Song-Song ;
Li, Yi-Zhi ;
Zheng, Li-Min .
INORGANIC CHEMISTRY, 2008, 47 (13) :5525-5527
[42]   The nature and geometry of intermolecular interactions between halogens and oxygen or nitrogen [J].
Lommerse, JPM ;
Stone, AJ ;
Taylor, R ;
Allen, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (13) :3108-3116
[43]   Synthesis, structure, and polymorphism studies in amine-templated open-framework zinc phosphites [J].
Mandal, Sukhendu ;
Natarajan, Srinivasan .
INORGANIC CHEMISTRY, 2008, 47 (12) :5304-5313
[44]  
McCrone W.C., 1965, PHYS CHEM ORGANIC SO, V2
[45]   Novel tools for visualizing and exploring intermolecular interactions in molecular crystals [J].
McKinnon, JJ ;
Spackman, MA ;
Mitchell, AS .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2004, 60 :627-668
[46]   Chemistry - Halogen versus hydrogen [J].
Metrangolo, P. ;
Resnati, G. .
SCIENCE, 2008, 321 (5891) :918-919
[47]   Halogen bonding based recognition processes: A world parallel to hydrogen bonding [J].
Metrangolo, P ;
Neukirch, H ;
Pilati, T ;
Resnati, G .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :386-395
[48]   Halogen bonding in supramolecular chemistry [J].
Metrangolo, Pierangelo ;
Meyer, Franck ;
Pilati, Tullio ;
Resnati, Giuseppe ;
Terraneo, Giancarlo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6114-6127
[49]   Halogen bonding in crystal engineering [J].
Metrangolo, Pierangelo ;
Resnati, Giuseppe ;
Pilati, Tullio ;
Biella, Serena .
HALOGEN BONDING: FUNDAMENTALS AND APPLICATIONS, 2008, 126 :105-136
[50]   Anion coordination and anion-templated assembly under halogen bonding control [J].
Metrangolo, Pierangelo ;
Pilati, Tullio ;
Terraneo, Giancarlo ;
Biella, Serena ;
Resnati, Giuseppe .
CRYSTENGCOMM, 2009, 11 (07) :1187-1196
12345678