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Characterization of Persistent Intramolecular C‐H⋅⋅⋅X(N,O) Bonds in Solid State and Solution
Author(s) -
Cappelli Andrea,
Giorgi Gianluca,
Anzini Maurizio,
Vomero Salvatore,
Ristori Sandra,
Rossi Claudio,
Donati Alessandro
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305680
Subject(s) - intramolecular force , carborane , hydrogen bond , crystallography , conformational isomerism , ring (chemistry) , boron , chemistry , amide , quinoline , molecule , ab initio , computational chemistry , solid state , stereochemistry , organic chemistry
The formation of intramolecular CH⋅⋅⋅X(N,O) bonds and their persistence in solution were studied by X‐ray crystallography and NMR techniques in two different rotamers of a molecule containing the ortho ‐carborane cage, an amide group and a quinoline ring. Experimental data were confirmed by theoretical ab initio calculations. From the resolved structure of the two forms of this potentially active drug for boron neutron capture therapy, accurate bonding and geometric parameters were extracted for this non‐classic hydrogen interaction, and their strength was calculated. These findings provided new insight in the theory of CH⋅⋅⋅X bonds, which appear stronger and less rare than it was previously thought.