DFT analysis of the nucleophilicity of substituted pyridines and prediction of new molecules having nucleophilic character stronger than 4-pyrrolidino pyridine

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• 作者：KAUSTAVMONI DEKA ; PRODEEP PHUKAN
• 关键词：Density functional theory ; nucleophilicity ; organo ; catalyst ; pyridine
• 刊名：Journal of Chemical Sciences
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：128
• 期：4
• 页码：633-647
• 全文大小：1,276 KB
• 参考文献：1.Ramsay W 1876 Phil. Mag. 2 269CrossRef
  2.Wu W, Kong H, Li H, Ho Y, Gao Y, Hao J, Murphy M B, Lam M H, Wong K and Lee C 2011 Eur. J. Org. Chem. 26 5054CrossRef
  3.Wu J, Kang S, Song B, Hu D, He M, Jin L and Yang S 2012 Chem. Central J. 62 8
  4.Di X, Liu Y, Liu Y, Yu X, Xiao H, Tian X and Gao R 2007 Pesticide Biochem. Physiol. 89 81CrossRef
  5.Dorn F, Pfiffner A and Schlageter M 1991 ACS Symposium Series 443 506CrossRef
  6.Lee L F, Stikes G L, Normansell J E, Molyneaux J M, Sing L Y L, Chupp J P, Parrish S K and Kaufmann J E 1991 ACS Symposium Series 443 195CrossRef
  7.Peine G, Hoffmann P, Seifert G and Schilling G 1985 Biochem. Physiol. Pflanzen 180 1CrossRef
  8.Harris R L N, Huppatz J L, Phillips J N and Teitei T 1979 In Advances in Pesticide Science H Geissbühler, G T Brooks and P C Kearney (Eds.) (Oxford: Pergamon) p. 99
  9.Willand-Charnley R, Fisher T J, Johnson B M and Dussault P H 2012 Org. Lett. 14 2242CrossRef
  10.Zhang Y, Zhang Y, Sun Y L, Du X, Shi J Y, Wang W D and Wang W 2012 Chem. Eur. J. 18 6328CrossRef
  11.Ko K, Nakano K, Watanabe S, Ichikawa Y and Kotsuki H 2009 Tetrahedron Lett. 50 4025CrossRef
  12.Xu X, Tang Z, Wang Y, Luo S, Cun L and Gong L 2007 J. Org. Chem. 72 9905CrossRef
  13.List B 2007 Chem. Rev. 107 5413CrossRef
  14.Cheong P H -Y, Legault C Y, Um J M, Cȩlebi-Ołcu̧m N and Houk K N 2011 Chem. Rev. 111 5042CrossRef
  15.De Rycke N, Couty F and David O R P 2011 Chem. Eur. J. 17 12852CrossRef
  16.Geerlings P, De Proft F and Langenaeker W 2003 Chem. Rev. 103 1793CrossRef
  17.Ingold C K 1934 Chem. Rev. 15 225CrossRef
  18.Swain C G and Scott C B 1953 J. Am. Chem. Soc. 75 141CrossRef
  19.Edwards J O 1954 J. Am. Chem. Soc. 76 1540CrossRef
  20.Edwards J O and Pearson R G 1962 J. Am. Chem. Soc. 84 16CrossRef
  21.Bunnett J F 1963 Ann. Rev. Phys. Chem. 14 271CrossRef
  22.Pearson R G, Sobel H and Songstad J 1968 J. Am. Chem. Soc. 90 319CrossRef
  23.Legon A C and Millen D J 1987 J. Am. Chem. Soc. 109 356CrossRef
  24.Legon A C and Millen D J 1987 Acc. Chem. Res. 20 39CrossRef
  25.Brotzel F, Kempf B, Singer T, Zipse H and Mayr H 2007 Chem. Eur. J. 13 336CrossRef
  26.De Rycke N, Berionni G, Couty F, Mayr H, Goumont R and David O R P 2011 Org. Lett. 13 530CrossRef
  27.Campodonico P, Santos J G, Andres J and Contreras R 2004 J. Phys. Org. Chem. 17 273CrossRef
  28.Contreras R, Andres J, Safont V S, Campodonico P and Santos J G 2003 J. Phys. Chem. A 107 5588CrossRef
  29.Chattaraj P K and Maiti B 2001 J. Phys. Chem. A 105 169CrossRef
  30.Pratihar S and Roy S 2010 J. Org. Chem. 75 4957CrossRef
  31.Pratihar S and Roy S 2011 Organometallics 30 3257CrossRef
  32.Domingo L R and Pérez P 2011 Org. Biomol. Chem. 9 7168CrossRef
  33.Campodónico P R and Aizman A 2006 Chem. Phys. Lett. 422 204CrossRef
  34.Deuri S and Phukan P 2012 Comput. Theor. Chem. 980 49CrossRef
  35.Soliman S M 2012 Comput. Theor. Chem. 994 105CrossRef
  36.Ess D H, Jones G O and Houk K N 2006 Adv. Synth. Catal. 348 2337CrossRef
  37.Chattaraj P K, Sarkar U and Roy D R 2006 Chem. Rev. 106 2065CrossRef
  38.Chattaraj P K and Roy D R 2007 Chem. Rev. 107 PR46CrossRef
  39.Chattaraj P K, Giri S and Duley S 2011 Chem. Rev. 111 PR43CrossRef
  40.Parr R G and Pearson R G 1983 J. Am. Chem. Soc. 105 7512CrossRef
  41.Parr R G, Von Szentpaly L and Liu S 1999 J. Am. Chem. Soc. 121 1922CrossRef
  42.Parr R G, Donnelly R A, Levy M and Palke W E 1978 J. Chem. Phys. 68 3801CrossRef
  43.Gázquez J L, Cedillo A and Vela A 2007 J. Phys. Chem. A 111 1966CrossRef
  44.Domingo L R, Chamorro E and Perez P 2008 J. Org. Chem. 73 4615CrossRef
  45.Kohn W and Sham L J 1965 Phys. Rev. 140 1133CrossRef
  46.Becke A D 1993 J. Chem. Phys. 98 5648CrossRef
  47.Lee C, Yang W and Parr R G 1988 Phys. Rev. B 37 785CrossRef
  48.Cohen A, Mori-Sánchez P and Yang W 2012 Chem. Rev. 112 289CrossRef
  49.Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Zakrzewski V G, Montgomery J A, Stratmann R E, Burant J C, Dapprich S, Millam J M, Daniels A D, Kudin K N, Strain M C, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson G A, Ayala P Y, Cui Q, Morokuma K, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Cioslowski J, Ortiz J V, Baboul A G, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin R L, Fox D J, Keith T, Al- Laham M A, Peng C Y, Nanayakkara A, Gonzalez C, Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Andres J L, Gonzalez C, Head Gordon M, Replogle E S and Pople J A 2004 GAUSSIAN 03, Revision E.01, (Gaussian Inc.: Wallingford, CT)
  50.Swain C G, Swain M S, Powell A L and Alunni S 1983 J. Am. Chem. Soc. 105 502CrossRef
  51.Um I -H, Lee E -J and Jeon S -E 2002 J. Phys. Org. Chem. 15 561CrossRef
  52.Kim Y, Cramer C J and Truhlar D G 2009 J. Phys. Chem. A 113 9109CrossRef
  53.Smith M B and March J 2007 In Advanced Organic Chemistry: Reactions, Mechanism and Structure 6 th edn., (Hoboken- New Jersey: John Wiley)
  
• 作者单位：KAUSTAVMONI DEKA (1)
  PRODEEP PHUKAN (1)
  
  1. Department of Chemistry, Gauhati University, Guwahati, 781 014, Assam, India
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  
• 出版者：Springer India
• ISSN：0973-7103

文摘

Some commonly used 3-substituted, 4-substituted and 3,4,5-substituted pyridines were examined using DFT to predict the nucleophilicity behavior based on four different methods known in the literature. HOMO-LUMO energy calculations were done using DFT/B3LYP/6-311G + (d,p) level of theory. To establish the most suitable nucleophilicity scale for all the ranges of pyridines covered herein, either Hammett substituent constant (σ) or experimental nucleophilicity values were computed. On the basis of this study, some new 4-substituted pyridines with enhanced nucleophilicity have been proposed. Nucleophilic behaviour of a few predicted molecules was found to be better than that of 4-pyrrolidino pyridine.