کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1406087 1501834 2010 11 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
The role of hydrogen bonding in conformational stabilization of 3,5,6- and 3,5-substituted (pyridin-2-yl)aminomethane-1,1-diphosphonic acids and related (pyrimidin-2-yl) derivative
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
The role of hydrogen bonding in conformational stabilization of 3,5,6- and 3,5-substituted (pyridin-2-yl)aminomethane-1,1-diphosphonic acids and related (pyrimidin-2-yl) derivative
چکیده انگلیسی

The crystal structures of three new members of the (pyridin-2-yl)aminomethane-1,1-diphosphonic acid (1-a) family are determined by X-ray diffraction and discussed with respect to molecular geometry and solid state organization.The striking structural feature of (3,5-dibromo-6-methylpyridin-2-yl)aminomethane-1,1-diphosphonic acid (2) and (3-chloro-5-trifluoromethylpyridin-2-yl)aminomethane-1,1-diphosphonic acid (3) is that regardless of a multiple substitution on the pyridyl ring the key factor for their conformational stabilization is the intramolecular N–H⋯X (X = Cl, Br) hydrogen bond involving substituent at 3-ring position.In contrast, the solid state conformation of (pyrimidin-2-yl)aminomethane-1,1-diphosphonic acid (4) is stabilized through intermolecular, bifurcated N–H⋯O hydrogen bonds, which is similar to that observed previously in 4- and 5-substituted Z-zwitterionic derivatives of (pyridin-2-yl)aminomethane-1,1-diphosphonic acid. Moreover, the 31P NMR spectra of 4 suggest similar dynamic process in solution, attributable to the rotation around the Cring–Namino bond. However, the rotational barrier in 4 is markedly lower as compared to 4- and 5-substituted (pyridin-2-yl)aminomethane-1,1-diphosphonic acids. This is attributed to low basicity of the nitrogen atom of the 1,3-diazinyl ring, which results in loss of conformational stabilization provided by intermolecular N–H⋯O hydrogen bonds in solution at low pH.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 980, Issues 1–3, 10 September 2010, Pages 182–192
نویسندگان
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