کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5376915 1504331 2006 11 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Structural features of neutral and protonated galanthamine: A crystallographic database and computational investigation
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی تئوریک و عملی
پیش نمایش صفحه اول مقاله
Structural features of neutral and protonated galanthamine: A crystallographic database and computational investigation
چکیده انگلیسی
The conformational preferences and structural features of neutral and protonated galanthamine have been investigated experimentally, using data retrieved from the CSD and PDB databases, and theoretically, through various quantum chemical calculations: HF/6-31++G(d,p), MPWB1K/6-31++G(d,p) and MP2/6-311++G(2d,p). The main characteristics of galanthamine: (i) the axial or equatorial orientation of the N-methyl substituent; (ii) the hydroxyl and methoxy groups orientations; (iii) the tetrahydroazepine ring conformation, have been investigated. It is found that galanthamine must exist as a mixture of axial and equatorial N-methyl isomers, the tetrahydroazepine ring adopting a chair conformation and the methoxy group being in trans position with respect to the dihydrofuran ring. In both chemical forms (neutral and protonated), the intramolecular OH…O hydrogen bonding conformation is preferred. Structural features of galanthamine appear very similar in both the gas phase and the solid state, whatever its chemical form, a trend that indicates the rigid character of the molecule.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Chemical Physics - Volume 328, Issues 1–3, 29 September 2006, Pages 307-317
نویسندگان
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