Synthesis and Theoretical Study of Intramolecular Hydrogen Bond at Two Possible Positions in Pyrazolo[1,2-b]phthalazine

作     者：Yoosefian,M. Raissi,H. Davamdar,E. Esmaeili,A.A. Azaroon,M. 

作者机构：Chemistry DepartmentBirjand UniversityBirjandIran Chemistry DepartmentSiastan and Balouchestan UniversityZahedanIran 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：2012年第30卷第4期

页      面：779-784页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201100036 or from the author 

主　　题：pyrazolo[ 1,2-b]phthalazine intramolecular hydrogen bond charge density 

摘      要：Properties of dimethyl 3-（alkylamino）-5,10-dioxo-5,10-dihydro-1H-pyraolo[1,20b]phthalazine-1,2-dicarboxy-late and its derivatives were studied by means of ab initio method. NO2 derivative of title compound was synthe- sized and the nature of its intramolecular hydrogen bond （HB） was investigated. Furthermore, the topological prop- erties of the electron density distributions for N--H＇＂O intramolecular bridges were analyzed in terms of the Bader theory of atoms in molecules （AIM）. The electron density （p） and Laplacian （V2p） properties, estimated by AIM calculations, indicated that O＇--H bond possesses low P and positive VZp values which are in agreement with elec- trostatic character of the HBs, whereas N--H bonds have covalent character （V2p〈0）. Moreover, steric effect of the t-Bu group on structure and topological parameters of pyrazolo[1,2-b]phthalazine conformers was studied. Fi- nally, the powerful method of Espinosa was used to obtain the H-bond energy.