Premium
Crystal Structures of Tetramesityl‐Substituted Tetracyclopenta[ def,jkl,pqr,vwx ]tetraphenylene
Author(s) -
Miyoshi Hirokazu,
Hisaki Ichiro,
Tobe Yoshito
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100503
Subject(s) - chemistry , antiaromaticity , molecule , crystallography , crystal structure , crystal (programming language) , benzene , perpendicular , bond length , derivative (finance) , molecular geometry , stereochemistry , aromaticity , geometry , organic chemistry , mathematics , computer science , financial economics , programming language , economics
Crystal structures of tetramesityl‐substituted tetracyclopenta[ def,jkl,pqr,vwx ]tetraphenylene (TCPTP) derivative were determined for crystals containing different solvents, CHCl 3 , CH 2 Cl 2 , acetone, and benzene at different temperatures to discuss the conjugation modes in the antiaromatic system, i. e., whether it adopts a D 2 h structure consisting of local aromatic sextets and quinodimethane substructures or a D 4 h double annulenenoid structure. The structures of the TCPTP core in all crystals determined at 113 K or 93 K resemble those of the theoretical D 2 h geometry, whereas the bond lengths at room temperature (293 K) adopt averaged values of the theoretical D 2 h and D 4 h geometries. These results are interpreted in terms of disorder of two perpendicularly oriented D 2 h structures at room temperature and support the theoretical prediction which favours the D 2 h geometry. The slightly different bond length distributions in the crystals are ascribed to the different space in the vicinity of the molecule which allows the molecule to adopt the two orientations in different occupancies.