intramolecular c-h···o hydrogen bonding in？1,4-dihydropyridine derivatives分子内碳氢键···o氢键 1,4-dihydropyridine衍生品.pdfVIP

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intramolecular c-h···o hydrogen bonding in？1,4-dihydropyridine derivatives分子内碳氢键···o氢键 1,4-dihydropyridine衍生品.pdf

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intramolecular c-h···o hydrogen bonding in？1,4-dihydropyridine derivatives分子内碳氢键···o氢键 1,4-dihydropyridine衍生品

Molecules 2011, 16, 8041-8052; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Intramolecular C-H···O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives Marina Petrova *, Ruslan Muhamadejev, Brigita Vigante, Brigita Cekavicus, Aiva Plotniece, Gunars Duburs and Edvards Liepinsh Latvian Institute of Organic Synthesis Aizkraukles 21 Street, Riga LV-1006, Latvia; E-Mails: muhamadejev@osi.lv (R.M.); vigante@osi.lv (B.V.); arkady@osi.lv (B.C.); aiva@osi.lv (A.P.); gduburs@osi.lv (G.D.); edv@osi.lv (E.L.) * Author to whom correspondence should be addressed; E-Mail: marina@osi.lv; Tel.: +371 Received: 26 July 2011; in revised form: 8 September 2011 / Accepted: 9 September 2011/ Published: 19 September 2011 Abstract: The diastereotopy of the methylene protons at positions 2 and 6 in 1,4- dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH···O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1 H-NMR spectra. Keywords: 1,4-dihydropyridines; bromination; nucleophilic substitution; hydrogen bond; NMR spectra; quantum chemical calculations 1. Introduction The 1,4-dihydropyridine (1,4-DHP) scaffold is a common component of pharmacologically active molecules which possess a variety of biological activities [1]. Several 1,4-DHP derivatives