Spectral LFER studies in some N-(substituted phenyl) formamides

Ganesamoorthy Thirunarayanan, Inasekaran Muthuvel, Vasudevan Sathiyendiran

Abstract


A series of N-(substituted phenyl) formamides were synthesised by sulphated titania (TiO2-SO4 2-) catalyzed formylation of substituted anilines and formic acid in acetonitrile medium at room temperature. The synthesised formamide derivatives are characterized by their spectral data. The infrared νNH, CO (cm-1) stretches, chemical shifts(δ, ppm) of NH, COH and ipso carbons(Ar-C-NH) were assigned and correlated with Hammett substituent constants using single and multi-regression analysis. From the results of statistical analyses, the effect of substituents on the spectral data have been studied.

Keywords


N-(Substituted phenyl)formamides; Sulphated titania(TiO2-SO4–-); IR and NMR spectra; Anilines; Hammett correlations.

Full Text:

PDF

References


B. C. Chen, M. S. Bednarz, R. Zhao, J. E. Sundeen, P. Chen, Z. Shen, A. P. Skoumbourdis, J.C. Barrish, Tetrahedron Lett., 41, 5453, (2000).

Voet and Voet, Fundamentals of Biochemistry, 3rd Edn, 2008, Wiley, New York.

J. B. Thoden, S. Firestine, A. Nixon, S. J. Benkovic, H. M. Holden, Biochem., 39, 8791, (2000).

K. Koayashi , S. Nagato, M. Kawakita, O. Morikawa, H. Konishi, Chem. Lett., 24, 575, (1995).

C. J. Gerack, L. M. White, Molecules., 19, 7689, (2014).

B. A. Aleiwi, K. Mitachi, M. Kurosu, Tetrahedron Lett., 54, 2077, (2013).

A. Deepali, A. Akansha, B. Anamika, K. Virendra Kumar, Res. J. Chem. Sci., 4, 54, (2014).

A. Chandra Shekar, A. Ravikumar, G. Sathaiah, V. Luke Paul, M. Sridhar, P. Shanthan Rao, Tetrahedron Lett. 50, 7099, (2009).

B. P. Bandgar, S. N. Kinkar, S. S. Chobe, G. G. Mandawad, O. S. Yemul, B. S. Dawane, Arch. Appl. Sci. Res., 3, 246, (2011).

K. P. Dhake, P. J. Tambade, R.S. Singhal, B. M. Bhanage, Green Chem Lett. Rev. 4, 151, (2011).

V. T. Kamble, G. M. Bondle, P. M. Pisal, Arabian J. Chem., Article in press, (2013): Doi: http://dx.doi.org/10.1016/j.arabjc. 2013.09.007.

J. Akbari, M. Hekmati, M. Sheykhan, A. Heydari, Arkivoc., 11, 123, (2009).

D. Yang, H. B. Jeon, Bull. Korean. Chem. Soc., 31, 1424, (2010).

S. H. Jung, J. H. Ahn, S. K. Park, J. K. Choi, Bull. Korean. Chem. Soc., 23, 149, (2002).

M. H. Sarvar, H. Sharghi, J. Org. Chem., 71, 6652, (2006).

M. I. Ansari, M. K. Hussain, N. yadav, P. K. Gupta, K. Hajela, Tetrahedron Lett., 3, 2063, (2012).

D. Habibi and M. Nasrollahzadeh, Comptus Rendus Chieme, 16, 1008, (2013).

D. Habibi, P. Rahmani, Z. Akbaripanah, J. Chem., (2013). Article ID 972960, DOI: http//:dx.doi.org/10.1153/2013/972960

S. M. Sajadi, M. Maham, A. Rezaei, Lett. Org. Chem., 11, 49, (2011).

S. Bahari, B. M. Aghdam, S. M. Sajadi, F. Seidali, Bull. Korean Chem. Soc. 33, 2251, (2012).

J. G. Kim, D. O. Jang, Synlett., 2093, (2010).

G. Brahmachari, S. Laskar, Tetrahedron Lett., 51, 2319, (2010).

P. Strazzoline, A. G. Giumanini, S. Cauci, Tetrahedron., 46, 1081, (1990).

F. F. Blicke, C. J. Lu, J. Am. Chem. Soc., 74, 3933, (1952).

J. Waki, J. Meienhofer, J. Org. Chem., 42, 2019, (1977).

F. M. F. Chen, N. L. Benoiton, Synthesis., 709, (1979).

H. L. Yale, J. Org. Chem. 36, 3238, (1971).

M. Miharam, Y. Ishino, S. Minakata, M. Komatsu, Synthesis., 15, 2317, (2003).

P. G. Reddy, G. D. K. Kumar, S. Baskaram, Tetrahedron., 41, 9149, (2000).

L. D. Luca, G. Giacomelli, A. Porcheddu, M. Salaris, Synlett., 2570, (2004).

O. Saidia, M. J. Bamford, A. J. Blackerc, J. Lyncha, S. P. Marsden, P. Plucinski, R. J. Watson, J. M. J. Williams, Tetrahedron Lett., 51, 5804, (2010).

M. Lei, L. Ma, L. Hua L., Tetrahedron Lett., 51, 4186, (2010).

B. Krishnakumar, M. Swaminathan, J. Mol. Catalysis A: Chem., 334, 98, (2011).

S. P. Pathare, R. V. Sawant, K. G. Akamanchi, Tetrahedron Lett., 53, 3259, (2012).

M R. P. Bhojegowd, A. Nizam, M. A. Pasha, Chin. J. Catal., 31, 518, (2010).

X. J. Yang, Y. S. Zhang, Res. Chem. Intermed., (2012). DOI. 10.1007/s11164-012-0803-7.

G. Thirunarayanan, M. Gopalakrishnan, G. Vanangamudi, Spectrochim. Acta., 67A, 1106, (2007).

R. Arulkumaran, G. Vanangamudi, D. Kamalakkannan, R. Sundararajan, S. Vijayakumar, K. Thirumurthy, P. Mayavel, G. Thirunarayanan, Annales, UMCS, 67(1-2), 45-77, (2012).

P. Janaki, K. G. Sekar, G. Thirunarayanan, J. Saudi Chem. Soc. (2013). Doi.10.1016/j.jscs.2012.11.013

G. Thirunarayanan, Int. Lett. Chem. Phys. Astro., 9(2), 152, (2013).

G. Thirunarayanan, G. Vanangamudi, V. Sathiyendiran, K. Ravi, Indian J. Chem., 50B, 593, (2011).

G. Vanangamudi, M. Subramanian, G. Thirunarayanan, Arabian J. Chem., (2013). DOI: 10.1016/j.arabjc.2013.03.006.

G. Thirunarayanan, K. G. Sekar, J. Taibah Univ. Sci., 8, 124, (2014).

Mayavel, G. Thirunarayanan, Annales-UMCS., 69(1-2), 160, (2014).

G. Thirunarayanan, I. Muthuvel, V. Sathiyendiran, Int. Lett. Chem. Phys. Astro., 9(2), 198, (2014).

G. Thirunarayanan, I. Muthuvel, V. Sathiyendiran, Int. Lett. Chem. Phys. Astro., 9(3), 114, (2015).

R. Senbagam, M. Rajarajan, R. Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi, G. Thirunarayanan, World Sci. News., 2, 211, (2015).

M. Rajarajan, R. Senbagam, R. Vijayakumar, V. Manikandan, S. Balaji, G. Vanangamudi, and G. Thirunarayanan, World Scientific News, 3, 155, (2015).

K. Ranganathan, R. Suresh, G. Vanangamudi, K. Thirumurthy, P. Mayavel, G. Thirunarayanan, Bull. Chem. Soc. Ethiop. 28(2), 271, (2014).

C. G. Swain, E. C. Lupton, J. Am. Chem. Soc. 90, 4328, (1968).




DOI: http://dx.doi.org/10.17951/aa.2015.70.2.31
Date of publication: 2016-02-15 12:20:02
Date of submission: 2016-02-15 10:40:02


Statistics


Total abstract view - 634
Downloads (from 2020-06-17) - PDF - 298

Indicators



Refbacks

  • There are currently no refbacks.


Copyright (c) 2016 Ganesamoorthy Thirunarayanan, Inasekaran Muthuvel, Vasudevan Sathiyendiran