Abstract
The interaction of external water molecules with hydrated pyrrole-2-carboxaldehyde PCL/(H2O) n complexes was investigated. The work was supported by both theoretical [DFT/TD-DFT methods using 6-311G++(d,p) basis set in the ground (S0) and excited (S1, S2, S3)states] and experimental [UV-Vis, FTIR and Raman] verification. The focus of the present work was on the weak intermolecular O–H⋯O, N–H⋯O–H hydrogen bonded interaction (IerHB) between PCL and external water molecules, and the influence of increasing the number of water molecules to form hydrated PCL/(H2O)n complexes. Effects were observed on different vibrational normal modes and on electronic transition levels. A hydrogen-bonded network of water induces a shift to higher energy in certain normal modes of PCL to form stable PCL/(H2O)n complexes by lowering the barrier energy. Potential energy distribution (PED) analysis indicates a significant charge transfer from PCL to water by creating a water bridge. Hydrogen bonding effects account for the substantial red shift and broadness in νNH, νCO vibrational modes. Water rearrangement turns out to be the main driving force for hydrated complex formation.
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Sahoo D, Adhikary T, Chowdhury P, Chakravorti S (2008) Theoretical study of excited state proton transfer in pyrrole-2-carboxylic acid. Molecular Phys 106:1441–1449
Mathew CV (2006) An efficient synthesis of highly substituted pyrroles from Β- oxodithiocarboxylates. Tetrahedron 62:1708–1716
Rice CA, Dauster I, Suhm MA (2007) Infrared spectroscopy of pyrrole-2-carboxaldehyde and its dimer: a planar Beta-sheet peptide model? J Phys Chem 126:134313
Subhasis P, Chowdhury P, Chakravorti S (2004) Modulation of complexation of 4 (1H-pyrrole 1-yl) benzoic acid with β-cyclodextrin in aqueous and non-aqueous environments. Chem Phys Lett 393:409–415
Leiserowitz L (1976) Structural crystallography and crystal chemistry. Acta Cryst B32:775–802
Singla N, Chowdhury P (2014) Nature of stokes shifted dual fluorescence in 2-acetyl-pyrrole: tuning between intramolecular hydrogen bonding and ESIPT pathways. Chem Phys Lett 612:25–32
Dubis AT, Grabowski SJ, Romanowska DB, Misiaszek T, Lestzczynski J (2002) Pyrrole-2-carboxylic acid and its dimers: molecular structures and vibrational spectrum. J Phys Chem A 106:10613–10621
Kumar N, Chakravorti S, Chowdhury P (2008) Experimental investigation by UV-VIS and IR spectroscopy to reveal electronic and vibrational properties of pyrrole-2-carboxyldehyde: a theoretical approach. J Mol Struct 891:351–356
Singla N, Chowdhury P (2013) Excited state behavior of pyrrole-2-carboxyldehyde: theoretical and experimental study. Spectrochim Acta A Mol Biomol Spectrosc 112:125–131
Pauling L, Marsh RE (1952) The structures of chlorine hydrate. Proc Natl Acad Sci USA 38:112–118
Szatyłowicz H, Sosnowska NS (2010) Characterizing the strength of individual hydrogen bonds in DNA base pairs. J Chem Inf Model 50:2151–2161
Yang Y, Arai T (1998) Novel photochemical behavior of olefin with a pyrrole ring and a phenanthroline ring controlled by hydrogen bonding. Tetrahedron Lett 39:2617–2620
Marstokk KM, Mollendal H (1974) Microwave spectrum, conformation, intramolecular hydrogen bond, and dipole moment of pyrrole-2-carboxaldehyde. J Mol Struct 23:93–101
Giuliano BM, Reva I, Fausto R (2010) Infrared spectra and photochemistry of matrix-isolated pyrrole-2-carbaldehyde. J Phys Chem A 114:2506–2517
Dubis AT (2014) Conformational preferences of 2-acylpyrroles in light of FT-IR and DFT studies. J Phys Chem Biophys 4:2161–0398
Nolasco MM, Amado AM, Ribeiro-Claro PJ (2006) Computationally-assisted approach to the vibrational spectra of molecular crystals: study of hydrogen-bonding and pseudo-polymorphism. Chem Phys Chem 7:2150–2161
Frisch MJ et al (2010) Gaussian 09, revision B.01. Gaussian Inc., Wallingford,
Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652
Becke AD (1997) Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J Chem Phys 107:8554–8560
Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B37:785–789
Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094
Robinson D, Besley NA, Lunt EA, O’Shea P, Hirst JD (2009) Electronic structure of 5-hydroxyindole: from gas phase to explicit solvation. J Phys Chem B 113:2535–2541
Dennington R, Keith T, Millam J (2007) Gauss View, version 4.1.2; Semichem, Shawnee Mission, KS
Jamroź MH (2004) Vibrational Energy Distribution Analysis VEDA 4, Warsaw
Gordon JJH (1996) Understanding the hydrogen bond using quantum chemistry. Acc Chem Res 29:536–543
Esseffar M, Firdoussi AE, Bouab W, Abboud JL, Mó O, Yáñez M (2009) Combined experimental and theoretical study on hydrogen-bonded complexes between cyclic ketones, lactones, and lactams with 3, 4-dinitrophenol. J Phys Chem A 113:14711–14717
Pal S, Kundu TK (2013) Stability analysis and frontier orbital study of different glycol and water complex. ISRN Phys Chem 2013:1–16
Clark T, Hennemann M, Murray JS, Politzer P (2007) Halogen bonding: the σ-hole. J Mol Model 13:291–296
Politzer P, Murray JS, Clark T (2015) Mathematical modeling and physical reality in noncovalent interactions. J Mol Model 21:52
Politzer P, Murray JS (2013) Halogen bonding: an interim discussion. Chem Phys Chem 14:278–294
Keresztury G (2002) Raman spectroscopy: theory. In: Chalmers JM, Griffith PR (eds) Handbook of vibrational spectroscopy. Wiley, New York
Arjunan V, Puviarasan N, Mohan S (2006) Fourier transform infrared and Raman spectral investigations of 5-aminoindole. Spectrochim Acta A 64:233–239
Singla N, Kumar R, Pathak A, Chowdhury P (2013) Excited state behavior of pyrrole 2-carboxyldehyde: theoretical and experimental study Spectrochim Acta A 112:125–131
Chandra S, Saleem H, Sundaraganesan N, Sebastian S (2009) The spectroscopic FT-IR gas phase, FT-IR, FT-Raman, polarizabilities analysis of Naphthoic acid by density functional methods. Spectrochim Acta A 74:704–713
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Rana, M., Chowdhury, P. Perturbation of hydrogen bonding in hydrated pyrrole-2-carboxaldehyde complexes. J Mol Model 23, 216 (2017). https://doi.org/10.1007/s00894-017-3380-2
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DOI: https://doi.org/10.1007/s00894-017-3380-2