Abstract
The geometries, energies, and IR characteristics of 1:1 noradrenaline–water (NA–H2O) complexes are studied at the ωB97XD/6-311++G(d,p) level. Various type of hydrogen bonds (H-bonds) are formed in these NA–H2O complexes, and the quantum theory of the atoms in molecules and natural bond orbital analyses are used to understand the nature of hydrogen bonding interactions. The intramolecular H-bond formed between the hydroxyl group and the amino N atom in free NA molecule is replaced by two intermolecular H-bonds and results in the formation of the most stable NA–H2O complex. In addition, the intramolecular H-bond keeps untouched in other NA–H2O complexes, moreover, it is strengthened by the intermolecular H-bonds in some NA–H2O complexes due to the cooperativity, whereas no such cooperativity is found in the other NA–H2O complexes in which the intermolecular H-bonds are away from the side chain of NA. Our researches show that the hydrogen bonding interaction is not the unique factor for the relative stabilities of NA–H2O complexes, and the structural deformation plays an important role as well.
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van Mourik T (2005) Chem Phys Lett 414:364
Snoek LC, van Mourik T, Carcabal P, Simons JP (2003) Phys Chem Chem Phys 5:4519
Miller TF, Clary DC (2004) J Phys Chem B 108:2484
Song YZ (2007) Spectrosc Acta A 67:1169
Perati PR, Cheng J, Jandik P, Hanko VP (2010) Electroanalysis 22:325
Dong H, Wang SH, Liu AH, Galligan JJ, Swain GM (2009) J Electroanal Chem 632:20
Luczak T (2009) Electroanalysis 12:1539
Seol H, Jeong H, Jeon S (2009) J Solid State Electrochem 13:1881
Yao H, Li SG, Tang YH, Chen Y, Chen YZ, Lin XH (2009) Electrochim Acta 54:4607
Yu ZY, Liu T, Guo DJ, Liu YJ, Liu CB (2010) J Mol Struct 984:402
Snoek LC, Van Mourik T, Simons JP (2003) Mol Phys 101:1239
van Mourik T (2004) Phys Chem Chem Phys 6:2827
Alonso JL, Sanz ME, Lopez JC, Cortijo V (2009) J Am Chem Soc 131:4320
Macleod NA, Simons JP (2006) Mol Phys 104:3317
Huang ZG, Dai YM, Yu L, Wang HK (2011) J Mol Model 17:2609
Benoit DM (2008) J Chem Phys 129:234304
Miller TF, Clary DC (2006) J Phys Chem A 110:731
Van Mourik T, Fruchtl HA (2005) Mol Phys 103:1641
Alagona G, Ghio C (2002) Int J Quantum Chem 90:641
Huang ZG, Dai YM, Yu L (2010) Struct Chem 21:863
Popelier PLA (2000) Atoms in molecules: an introduction. Prentice Hall, London
Matta CF, Boyd RJ (2007) The quantum theory of atoms in molecules: from solid state to DNA and drug design. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Bader RFW (1990) Atoms in molecules: a quantum theory. Oxford University Press, Oxford
Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899
Reed AE, Weinhold F, Curtiss LA, Pochatko DJ (1986) J Chem Phys 84:5687
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009). Gaussian, Inc., Wallingford
Chai JD, Head-Gordon M (2008) Phys Chem Chem Phys 10:6615
McLean AD, Chandler GS (1980) J Chem Phys 72:5639
Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650
Rao L, Ke HW, Fu G, Xu X, Yan YJ (2009) J Chem Theory Comput 5:86
Huang ZG, Dai YM, Wang HK, Yu L (2011) J Mol Model 17:2781
Huang ZG, Yu L, Dai YM (2011) Int J Quantum Chem 111:3915
Huang ZG, Yu L, Dai YM, Wang HK (2011) Struct Chem 22:57
Boys SF, Bernardi F (1970) Mol Phys 19:553
Biegler-König F, Schönbohm J (2000) University of Applied Sciences, Bielefeld
Yu ZY, Guo DJ, Wang HQ (2004) Chin J Chem Phys 17:149
Millefiori S, Raudino A, Zuccarello F (1980) Z Phys Chem Neue Folge 123:67
Bondi A (1964) J Phys Chem 68:441
Galvez O, Gomez PC, Pacios LF (2003) J Chem Phys 118:4878
Miao R, Jin C, Yang GS, Hong J, Zhao CM, Zhu LG (2005) J Phys Chem A 109:2340
Nozad AG, Meftah S, Ghasemi MH, Kiyani RA, Aghazadeh M (2009) Biophys Chem 141:49
Parreira RLT, Valdes H, Galembeck SE (2006) Chem Phys 331:96
Zhou HW, Lai WP, Zhang ZQ, Li WK, Cheung HY (2009) J Comput Aided Mol Des 23:153
Koch U, Popelier PLA (1995) J Phys Chem 99:9747
Arnold WD, Oldfield E (2000) J Am Chem Soc 122:12835
Pacios LF (2004) J Phys Chem A 108:1177
Alkorta I, Rozas I, Elguero J (1998) Chem Soc Rev 27:163
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This study is supported by Tianjin Science and Technology Development Fund Projects in Colleges and Universities (No. 20080504).
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Wang, H., Huang, Z., Shen, T. et al. Theoretical study on the hydrogen bonding interactions in 1:1 supermolecular complexes of noradrenaline with water. Struct Chem 23, 1163–1172 (2012). https://doi.org/10.1007/s11224-011-9940-7
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DOI: https://doi.org/10.1007/s11224-011-9940-7