Abstract
A theoretical study of structural, electronic, topological and vibrational parameters of the ternary hydrogen-bonded complexes C2H4O···2HF, C2H5N···2HF and C2H4S···2HF is presented here. Different from binary systems with a single proton donor, the tricomplexes have the property of forming multiple hydrogen bonds, which are analyzed from a structural and vibrational point of view, but verified only by means of the quantum theory of atoms in molecules (QTAIM). As traditionally done in the hydrogen bond theory, the charge transfer between proton donors and acceptors was computed using the CHELPG calculations, which also revealed agreement with dipole moment variation and a cooperative effect on the tricomplexes. Furthermore, redshift events on proton donor bonds were satisfactorily identified, although, in this case, an absence of experimental data led to the use of a theoretical argument to interpret these spectroscopic shifts. It was therefore the use of the QTAIM parameters that enabled all intermolecular vibrational modes to be validated. The most stable tricomplex in terms of energy was identified via the strength of the hydrogen bonds, which were modeled as directional and bifurcated.
Similar content being viewed by others
References
Acheson RM (1976) An introduction to the chemistry of heterocyclic compounds. Wiley, New York
Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds)(1995–2007) Comprehensive heterocyclic chemistry III. Elsevier, Amsterdam
Christl M, Leininger H, Brunn E (1982) J Org Chem 47:661–666
Singh MM, Angelici RJ (1984) Inorg Chem 23:2691–2698
Bertani R, Mozzon M, Michelin RA (1988) Inorg Chem 27:2809–2815
Lukevits É (1994) Chem Heterocycl Compd 30:11–12
Salimon J, Salih N, Hussien, Yousif E (2009) Eur J Sci Res 31:256–264
Banks HD, White WE (2001) J Org Chem 66:5981–5986
Araújo OBG, RCMU CAB, Ramos MN (2007) J Theor Comput Chem 6:647–660
Araújo OBG, RCMU CAB, Ramos MN (2009) Struct Chem 20:663–670
Oliveira BG, Araújo RCMU, Carvalho AB, Ramos MN, Hernandes MZ, Cavalcante KR (2007) J Mol Struct THEOCHEM 802:91–97
Kojić-Prodić B, Molčanov K (2008) Acta Chim Slov 55:692–708
Oliveira BG, Araújo RCMU, Carvalho AB, Ramos MN (2009) J Mol Model 15:123–131
Desiraju GR (2010) Angew Chem Int Ed 49:2–10
Custelcean R, Jackson JE (2001) Chem Rev 101:1963–1980
Tubergen MJ, Andrews AM, Kuczkowski RL (1993) J Phys Chem 97:7451–7457
Fowler PW, Legon AC, Thumwood JMA, Waclawik ER (2000) Coord Chem Rev 197:231–247
Antolínez S, Gerbi M, López LC, Alonso JL (2001) Phys Chem Chem Phys 3:796–799
Goswami M, Arunan E (2009) Phys Chem Chem Phys 11:8974–8983
Leung HO, Marshall MD, Drake TL, Pudlik T, Savji N, McCune DW (2009) J Chem Phys 131:204301–204308
Møllendal H, Konovalov A, Guillemin JC (2010) J Phys Chem A 114:5537–5543
Cooke AS, Corlett GK, Legon AC (1998) Chem Phys Lett 291:269–276
Cole CG, Legon AC (2004) Chem Phys Lett 400:419–424
Arunan E, Dev S, Mandal PK (2004) App Spec Rev 39:131–181
Maris A, Ottaviani P, Caminati W (2002) Chem Phys Lett 360:155–160
Oliveira BG, Pereira FS, Araújo RCMU, Ramos MN (2006) Chem Phys Lett 427:181–184
Del Bene JA (1996) Mol Phys 89:47–59
Oliveira BG, Araújo RCMU, Carvalho AB, Lima EF, Silva WLV, Ramos MN, Tavares AM (2006) J Mol Struct THEOCHEM 755:39–45
Gershinowitz H, Eyring H (1935) J Am Chem Soc 57:985–991
Rozenberg BA (1986) Adv Polymer Sci 75:113–165
Jursic BS (1998) J Mol Struct THEOCHEM 434:37–42
Oliveira BG, Araújo RCMU, Chagas FF, Ramos MN (2008) J Mol Model 14:949–955
Legon AC, Thorn JC (1994) Chem Phys Lett 227:472–479
Legon AC (1995) Chem Phys Lett 247:24–31
Oliveira BG, Vasconcellos MLAA (2006) J Mol Struct THEOCHEM 774:83–88
Oliveira BG, Leite LFCC (2009) J Mol Struct THEOCHEM 915:38–42
Legon AC, Wallwork AL, Millen DJ (1991) Chem Phys Lett 178:279–284
Oliveira BG, Araújo RCMU, Carvalho AB, Ramos MN (2009) J Mol Model 15:421–432
Geerlings P, De Proft F, Langenaeker W (2003) Chem Rev 103:1793–1873
Bader RFW (1991) Chem Rev 91:893–928
Oliveira BG, Araújo RCMU, Pereira FS, Lima EF, Silva WLV, Carvalho AB, Ramos MN (2008) Quim Nova 31:1673–1679
Rao L, Ke H, Fu G, Xu X, Yan Y (2009) J Theor Comput Chem 5:86–96
Becke AD (1993) J Chem Phys 98:5648–5652
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789
Oliveira BG, Araújo RCMU, Carvalho AB, Ramos MN (2007) Chem Phys Lett 433:390–394
Oliveira BG, Santos ECS, Duarte EM, Araújo RCMU, Ramos MN, Carvalho AB (2005) Spectrochim Acta A 60:1883–1887
Bader RFW (1991) Atoms in molecules. A quantum theory. Clarendon, Oxford
Bone RGA, Bader RFW (1996) J Phys Chem 100:10892–10911
Filho EBA, Ventura E, do Monte SA, Oliveira BG, Junior CGL, Rocha GB, Vasconcellos MLAA (2007) Chem Phys Lett 449:336–340
Ren F-D, Cao D-L, Wang W-L, Ren J, Hou S-Q, Chen H-S (2009) J Mol Model 15:515–523
Risikrishna Varadwaj PR (2010) J Mol Model 16:965–974
Oliveira BG, Araújo RCMU, Ramos MN (2008) Struct Chem 19:185–189
Oliveira BG, Vasconcellos MLAA, Olinda RR, Filho EBA (2009) Struct Chem 20:81–90
Oliveira BG, Araújo RCMU, Ramos MN (2008) Struct Chem 20:665–670
Oliveira BG, Vasconcellos MLAA (2009) Inorg Chem Commun 12:1142–1144
Smith DA (1994) ACS Symp Ser 569:1–5
Olovsson I (2006) Z Phys Chem 220:963–978
Ratajczak H, Orville-Thomas WJ, Rao CNR (1976) Chem Phys 17:197–216
Dognon J-P, Durand S, Granucci G, Lévy B, Millié P, Rabbe C (2000) J Mol Struct THEOCHEM 507:17–23
Carbó-Dorca R, Bultinck P (2004) J Math Chem 36:231–239
Breneman CM, Wiberg KB (1990) J Comput Chem 11:361–373
Cioslowski J, Hamilton T, Scuseria G, Hess BA Jr, Hu J, Schaad LJ, Dupuis M (1990) J Am Chem Soc 112:4183–4186
Oliveira BG, Araújo RCMU, Ramos MN (2010) J Mol Struct THEOCHEM 944:168–172
Talaty ER, Simons G (1978) Theor Chim Acta 48:331–335
Grigorenko BL, Nemukhin AV, Apkarian VA (1997) J Chem Phys 108:4413–4425
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery Jr JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Rega N, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98W, revision A.1. Gaussian Inc., Pittsburgh
Cioslowski J (1992) Chem Phys Lett 194:73–78
Cioslowski J (1992) Chem Phys Lett 219:151–154
Cioslowski J, Nanayakkara A, Challacombe M (1993) Chem Phys Lett 203:137–142
Biegler-König F (2002) AIM 2000 1.0 program. University of Applied Sciences, Bielefeld
Gilli P, Bertolasi V, Ferretti V, Gilli G (1994) J Am Chem Soc 116:909–915
Grabowski SJ, Sokalski WZ, Leszczynski J (2006) J Phys Chem A 110:4772–4779
Oliveira BG, Santos ECS, Duarte EM, Araújo RCMU, Ramos MN, Carvalho AB (2004) Spectrochim Acta A 60:1883–1887
Oliveira BG, Duarte EM, Araújo RCMU, Ramos MN, Carvalho AB (2005) Spectrochim Acta A 61:491–494
Oliveira BG, Araújo RCMU, Ramos MN, Carvalho AB (2007) J Theor Comput Chem 6:647–660
Grabowski SJ (2009) Croat Chim Acta 82:185–192
Majerz I (2007) Mol Phys 105:2305–2314
Martin TW, Derewenda ZS (1999) Nat Struct Biol 6:403–406
Oliveira BG, Araújo RCMU, Ramos MN, Carvalho AB (2007) Quim Nova 30:1167–1170
Van Meerssche M, Feneau-Dupont J (1976) Introduction à la cristallographie et à la chimie structurale. Oyez é editeur, Leuven
Oliveira BG, Vasconcellos MLAA (2009) Acta Chim Slov 56:340–344
Oliveira BG, Araújo RCMU, Carvalho AB, Ramos MN (2007) Spectrochim Acta A 68:626–631
Pople JA, Frisch MJ, Del Bene JE (1982) Chem Phys Lett 91:185–189
Araújo RCMU, Silva JBP, Ramos MN (1995) Spectrochim Acta A 51:821–830
Araújo RCMU, Ramos MN (1996) J Mol Struct THEOCHEM 366:233–240
Deakyne CA, Cravero JP, Hobson WS (1984) J Phys Chem 88:5975–5981
Parra RD, Bulusu S, Zeng XC (2003) J Chem Phys 118:3499–3509
Karpfen A (1997) Molecular interactions. Wiley, New York
King BF, Weinhold F (1995) J Chem Phys 103:333–348
Suhai S (1994) J Chem Phys 101:9766–9783
Berashevich JA, Chakraborty T (2007) Chem Phys Lett 446:159–164
Oliveira BG, Araújo RCMU (2007) Quim Nova 30:791–796
Ratajczak H (1972) J Phys Chem 76:3000–3004
Ratajczak H, Orville-Thomas WJ (1975) J Mol Struct 26:387–391
Allen AC (1975) Proc Nat Acad Sci USA 72:4701–4705
Nesbitt DJ (1988) Chem Rev 88:843–870
Swanepoel J, Heyns AM (1990) Spectrochim Acta A 46:1629–1638
Araújo RCMU, Ramos MN (1998) J Braz Chem Soc 9:499–505
Oliveira BG, Araújo RCMU, Ramos MN (20097) J Mol Struct THEOCHEM 908:79-83
Hobza P, Havlas Z (2000) Chem Rev 100:4253–4264
Biswal HS, Chakraborty S, Wategaonkar S (2008) J Chem Phys 129:184317–184321
Rozenberg M, Loewenschuss A, Marcus Y (2000) Phys Chem Chem Phys 2:2699–2702
Dinadayalane TC, Leszczynski J (2009) J Chem Phys 130:81101–81105
Cézard C, Rice CA, Suhm MA (2006) J Phys Chem A 110:9839–9848
Borowski P, Pilorz K, Pitucha M (2010) Spectrochim Acta A 75:1470–1475
Freed KF (1971) Ann Rev Phys Chem 22:313–346
Bader RFW (2009) J Phys Chem A 113:10391–10396
Bader RFW (1998) J Phys Chem A 102:7314–7323
Bader RFW (1991) Chem Rev 91:893–928
Bader RFW, Beddall PM, Peslak J Jr (1973) J Chem Phys 58:557–566
Vila A, Mosquera RA (2007) Chem Phys Lett 443:22–28
Gnecco D, Laura Orea F, Galindo A, Enríquez RG, Toscano RA, Reynolds WR (2000) Molecules 5:998–1003
Watson IDG, Yudin AK (2003) J Org Chem 68:5160–5167
Hu XE (2004) Tetrahedron 60:2701–2743
Schneider C (2009) Angew Chem Int Ed 48:2082–2084
Seki K, Yu R, Yamazaki Y, Yamashita Y, Kobayashi S (2009) Chem Commun 5722–5724
Giguere PA, Turrell S (1980) J Am Chem Soc 102:5473–5477
Tamamura H, Yamashita M, Muramatsu H, Ohno H, Ibuka T, Otaka A, Fujii N (1997) Chem Comm 3227–3228
Oliveira BG, Vasconcellos MLAA, Olinda RR, Filho EBA (2009) Struct Chem 20:897–902
Babkov LM, Baran J, Davydova NA, Uspenskiy KE (2006) J Mol Struct 792–793:68–72
Dimitrova Y (2004) Spectrochim Acta A 60:3049–3057
Grabowski SJ (2000) J Mol Struct 553:151–156
Grabowski SJ (2001) J Mol Struct 562:137–143
Wojtulewski S, Grabowski SJ (2002) J Mol Struct 605:235–240
Wojtulewski S, Grabowski SJ (2003) Chem Phys Lett 378:388–394
Savatinova I, Anachkova E (1983) Phys Stat Solidi 120:539–545
Unterderweide K, Engelen B, Boldt K (1994) J Mol Struct 322:233–239
Oliveira BG, Araújo RCMU, Ramos MN (2010) Quim Nova 33:1155–1162
Koritsanszky T (2006) Chapter 12. In: Hydrogen bonds—new insights. Springer, Berlin, pp 441–470
Herrebout WA, Stolov AA, van der Veken BJ (2001) J Mol Struct 563–564:221–226
Parra RD, Furukawa M, Gong B, Zeng XC (2001) J Chem Phys 115:6030–6035
Araújo RCMU, Soares VM, Oliveira BG, Lopes KC, Ventura E, do Monte SA, Santana OL, Carvalho AB, Ramos MN (2006) Int J Quantum Chem 106:2714–2722
Van Duijneveldt FB, van Duijneveldt-van de Rijdt JGCM, van Lenthe JH (1994) Chem Rev 94:1873–1885
Oliveira BG, Araújo RCMU, Leite ES, Ramos MN (2011) Int J Quantum Chem 111:111–116
Acknowledgments
The authors would like to thank the Brazilian funding agencies Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Oliveira, B.G., Araújo, R.C.M.U., Carvalho, A.B. et al. Hydrogen bonds determine the structures of the ternary heterocyclic complexes C2H4O···2HF, C2H5N···2HF and C2H4S···2HF: density functional theory and topological calculations. J Mol Model 17, 2847–2862 (2011). https://doi.org/10.1007/s00894-011-0969-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00894-011-0969-8