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Stereoselective Synthesis , Structural and Spectroscopic Study of 4,5,11‐Triazatricyclo[6.2.1.0*2,6*]Undec‐5‐ene
Author(s) -
Mabied Ahmed F.,
Girgis Adel S.,
Shalaby ElSayed M.,
George Riham F.,
ElGendy Bahaa ElDien M.,
Baselious Fady N.
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2440
Subject(s) - chemistry , triclinic crystal system , molecular orbital , crystallography , atomic orbital , crystal structure , intermolecular force , electrophile , computational chemistry , molecular geometry , stereochemistry , molecule , organic chemistry , physics , quantum mechanics , catalysis , electron
3‐(2,4‐Dichlorophenyl)‐7‐[(2,4‐dichlorophenyl)methylidene]‐11‐methyl‐4‐phenyl‐4,5,11‐triazatricyclo[6.2.1.0*2,6*]undec‐5‐ene ( 3 ) was synthesized in a stereoselective manner. Single crystal X‐ray study of 3 revealed that the structure belongs to the triclinic system with space group P 1 ¯ . The structure is further stabilized by an intermolecular CH … π interaction. Molecular mechanics force field (MM + ), followed by either semi‐empirical AM1 or PM3, was used to calculate the optimized geometrical parameters of 3 . The determined theoretical geometry parameters were found to be in good agreement with the parameters obtained by a single‐crystal study. Vibrational frequencies and gauge‐independent atomic orbital, 1 H‐NMR and 13 C‐NMR chemical shifts were computed at B3LYP/6‐31G(d) level of theory. Moreover, the molecular electrostatic potential of 3 has been calculated exhibiting that the most electrophilic site of 3 is the N‐3 atom; however, the nucleophilic site is distributed on the H atoms of dichlorophenyl groups. The frontier molecular orbitals of 3 have been determined by the same technique.