Premium
Chemistry of the phenoxathiins and isosterically related heterocycles. XVI . The synthesis and molecular structure of 3‐azaphenoxathiin: Evidence in support of factors responsible for control of the dihedral angle
Author(s) -
Caldwell Steven R.,
Martin Gary E.,
Simonsen Stanley H.,
Inners Ruth R.,
Willcott M. Robert
Publication year - 1981
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.5570180308
Subject(s) - dihedral angle , chemistry , nitrogen atom , ring (chemistry) , crystallography , atom (system on chip) , crystal structure , computational chemistry , molecule , organic chemistry , hydrogen bond , computer science , embedded system
The synthesis of the 3‐azaphenoxathiin ring system and its molecular structure are reported. Based on 13 C‐nmr chemical shift additivities associated with the insertion of an annular nitrogen atom and the observed 13 C‐nmr shift of Cα, the title compound was predicted to have a dihedral angle θ = 160.2°. The observed dihedral angle from the crystal structure was found to be θ = 167.07° which is in reasonably good agreement with the predicted value. It is proposed that the position of the annular nitrogen atom is solely in‐control of the observed dihedral angle.