Nuclear magnetic resonance and molecular modeling study of exocyclic carbon–carbon double bond polarization in benzylidene barbiturates
作者： J. Daniel Figueroa-Villar , Andreia A. Vieira
DOI: 10.1016/J.MOLSTRUC.2012.09.021
关键词:
摘要: Abstract Benzylidene barbiturates are important materials for the synthesis of heterocyclic compounds with potential development new drugs. The reactivity benzylidene is mainly controlled by their exocyclic carbon–carbon double bond. In this work, bond polarization was estimated experimentally NMR and correlated Hammett σ values aromatic ring substituents molecular modeling calculated atomic charge difference. It demonstrated that carbon chemical shift differences NBO can be used to predict reactivity.
harvard.edu
elsevier.com
sci-hub.se 参考文章(27)
Marcos Caroli Rezende, Iriux Almodovar, Substituent electrophilicities in the NMR spectra of barbituric derivatives Magnetic Resonance in Chemistry. ,vol. 50, pp. 266- 270 ,(2012) , 10.1002/MRC.2858
Pornpun Rattananakin, Charles U. Pittman, Willard E. Collier, Svein Saebø, Ab initio studies of push–pull systems Structural Chemistry. ,vol. 18, pp. 399- 407 ,(2007) , 10.1007/S11224-006-9140-Z
José Daniel Figueroa-Villar, Elizabete R. Cruz, A simple approach towards the synthesis of oxadeazaflavines Tetrahedron. ,vol. 49, pp. 2855- 2862 ,(1993) , 10.1016/S0040-4020(01)80384-7
Andreia A Vieira, Niele M Gomes, Maria E Matheus, Patricia D Fernandes, José D Figueroa-Villar, Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants Journal of the Brazilian Chemical Society. ,vol. 22, pp. 364- 371 ,(2011) , 10.1590/S0103-50532011000200024
G. Fischer, W.-D. Rudorf, E. Kleinpeter, Study of the distribution of the π-electrons in push-pull alkenes by 1H and 13C NMR spectroscopy Magnetic Resonance in Chemistry. ,vol. 29, pp. 212- 222 ,(1991) , 10.1002/MRC.1260290305
Khalid M Khan, Muhammad Ali, Asma Ajaz, Shahnaz Perveen, M Iqbal Choudhary, None, Synthesis of 5-Arylidene Barbiturates: A Novel Class of DPPH Radical Scavengers Letters in Drug Design & Discovery. ,vol. 5, pp. 286- 291 ,(2008) , 10.2174/157018008784619889
Florian Seeliger, Stefan T. A. Berger, Grygoriy Y. Remennikov, Kurt Polborn, Herbert Mayr, Electrophilicity of 5-Benzylidene-1,3-dimethylbarbituric and -thiobarbituric Acids The Journal of Organic Chemistry. ,vol. 72, pp. 9170- 9180 ,(2007) , 10.1021/JO071273G
R Benassi, C Bertarini, E Kleinpeter, F Taddei, Exocyclic push–pull conjugated compounds. Part 2. The effect of donor and acceptor substituents on the rotational barrier of push–pull ethylenes Journal of Molecular Structure-theochem. ,vol. 498, pp. 217- 225 ,(2000) , 10.1016/S0166-1280(99)00276-6
Yuelian Xu, William R Dolbier, Synthesis of novel fluorinated derivatives of 1,3-dimethylbarbituric acid Tetrahedron. ,vol. 54, pp. 6319- 6328 ,(1998) , 10.1016/S0040-4020(98)00329-9
Issa Yavari, Mehdi Adib, Hamid R. Bijanzadeh, Majid M. M. Sadegi, Hossein Logmani-Khouzani, Javad Safari, Rotational Energy Barrier of the Polarized Carbon–Carbon Double Bond in Quinophthalone Monatshefte Fur Chemie. ,vol. 133, pp. 1109- 1113 ,(2002) , 10.1007/S007060200081