Abstract
In the present work, the absorption and fluorescence spectra of newly synthesized aryl boronic acid derivative namely 2-Methylphenyl boronic acid (2MPBA) have been recorded in various solvents of different polarities. The ground state dipole moment of 2MPBA was obtained from quantum chemical calculations. Solvatochromic correlations were used to estimate the ground state (μ g ) and excited state (μ e ) dipole moments. The excited state dipole moments are observed to be greater than the ground state dipole moment and ground and excited state dipole moments are not parallel but subtend by an angle of 880. Further, the changes in dipole moment (Δμ) were calculated both from solvatochromic shift method and microscopic solvent polarity parameter (E N T ), and the value are compared. The spectral variations were analyzed by Kamlet-Taft parameters.
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Chaofeng D, Yunfeng C, Jianmei C, Binghe W (2010) Molecules 15:5768–5781
Dennis G. Hall, Boronic acids: preparation and applications in organic synthesis 2nd completely revised edition (2011)
Lackowicz JR (1983) Principle of fluorescence spectroscopy. Plenum Press, New York
K. K. Rohtagi–Mukherjee Fundamentals of Photochemistry, Wiley Eastern Ltd., (1992)
Koutek B (1978) Collect Czech Chem Commun 43:2368–2386
Kawski A, Kuklinski B, Bojarski P (2007) Chem Phys Lett 448:208–212
Raikar US, Renuka CG, Nadaf YF, Mulimani BG, Karguppikar AM, Soudagar MK (2006) Spectrochim Acta A 65:673–677
Biradar DS, Siddlingeshwar B, Hanagodimath SM (2008) J Mol Struct 875:108–112
Lippert E (1957) Z Elektrochem 61:962–975
Bakshiev NG (1964) Opt Spectrosk 16:821–832
L. Bilot, A. Kawski, Z. Naturforsch. 18A (1963) 10–256
L. Bilot, A. Kawski, Z. Naturforsch. 17A (1962) 621–627
Chamma A, Viallet P, Acad CR (1970) Sci Paris Ser C 270:1901–1904
Katritzky AR, Fara DC, Yang H, Tamm K, Tamm T, Karelson M (2004) Chem Rev 104(1):175–198
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, 1988.
Raveendra M, Melavanki NR, Patil SB, Kapatkar NH, Ayachit SU, Thipperudrappa J, Nataraju AR (2011) J Mol Liq 2:105–110
Raveendra M, Melavanki HD, Patil SU, Kadadevarmath JS (2012) J Fluoresc 22:137–144
Patil NR, Melavanki RM, Chougala BM, Shastri LA, Sanningannavar FM (2012) Int J Life Sc Pharm & Sci 2(2):139–149
Nagaraja D, Patil NR, Kusanur RA, Patil HD, Melavanki RM (2013) Int J Life Sc Pharm & Sci 3(1):54–64
Patil SN, Sanningannavar FM, Navati BS, Patil NR, Kusanur RA, Melavanki RM (2014) Int J Life Sc Pharm & Sci 4(1):12–20
Patil NR, Melavanki RM, Kapatkar SB, Ayachit NH, Saravanan J (2011) J Flurosec 21:1213–1222
Kadadevarmath JS, Malimath GH, Patil NR, Geethanjali HS, Melavanki RM (2013) Can J Phys 91:1107–1113
Thipperudrappa J (2014) Mapana J Sci 14(1):103–119
Thipperudrappa J, Biradar DS, Manohara SR, Hanagodimath SM, Inamadar SR, James RM (2008) Spectrochim Acta A Part A 69(3):991–997
Raikar US, Tangod VB, Mastiholi BM, Sreenivasa S (2010) Afr J Pure and Appl Chem 4(9):188–197
Nagachandra KH, Mannekutla JR, Amarayya SM, Inamdar SR (2012) Eur J Chem 3(2):163–171
Joshi S, Pant DD (2012) J Mol Liq 166:49–52
Sıdır YG, Sıdır I (2013) Spectrochim Acta A 102:286–296
Jayabharathi J, Thanikachalam V, Srinivasan N, Venkatesh M (2012) Spectrochim Acta A 90:125–130
Zakerhamidi MS, Ahmadi-Kandjani S, Moghadam M, Ortyl E, Kucharski S (2011) J Mol Struc 996:95–100
Gilani G, Hosseini SE, Moghadam M, Alizadeh E (2012) Spectrochim Acta A 89:231–237
Kawaski A (1992) In: Rabeck JF (ed) Photochem and Photophys, 5th edn. CRC Press, Boca Raton, Ann Arbor Boston, pp 1–47
Kawaski A (1966) Acta Phys Polon 29:507–518
Reichardt C (1994) Chem Rev 94:2319–2358
Ravi M, Soujnya T, Samanta A, Radhakrishnan TP, Chem J (1995) Soc Faraday Trans 91:2739–2742
Kamlet MJ, Abboud JLM, Abraham MH, Taft RW (1983) J Org Chem 48:2877–2887
Molander GA, Trice SLJ, Dreher SD (2010) J Am Chem Soc 132(50):17701–17703
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Authors (GVM) and (NRP) thank the H.O.D., the Principal B V B College of Engineering & Technology, Hubli, India for financial support under Capacity Building Fund and K.L.E Society Management Belgaum for their encouragement. And another author (RMM) is also grateful to the H.O.D., Dr. Suguna, the Principal and the Management of M.S.R.I.T. for their continuous encouragement.
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Muddapur, G.V., Patil, N.R., Patil, S.S. et al. “Estimation of Ground and Excited State Dipole Moments of aryl Boronic acid Derivative by Solvatochromic Shift Method”. J Fluoresc 24, 1651–1659 (2014). https://doi.org/10.1007/s10895-014-1452-6
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DOI: https://doi.org/10.1007/s10895-014-1452-6