Competing hydrogen bond topologies in 2-fluoroethanol dimer

Journal of Molecular Structure

Volumn 786, Issue 2-3 SPEC. ISS., 2006, Pages 86-95

  Scharge, Tina ^a   Emmeluth, Corinna ^a   Häber, Thomas ^a   Suhm, Martin A ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Chirality; Conformation; FT IR; H bond; Jet; Relaxation

Indexed keywords

CONFORMATIONS; DIMERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; ISOMERS; JETS; MOLECULAR ORIENTATION; STEREOCHEMISTRY;

CHIRALITY; CONFORMATION; H-BOND; RELAXATION;

HYDROGEN BONDS;

EID: 33645679962     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2005.09.022     Document Type: Article

References (35)

1. Coussan S., Alikhani M.E., Perchard J.P., and Zheng W.Q. Infrared-induced isomerization of ethanol dimers trapped in argon and nitrogen matrices: Monochromatic irradiation experiments and DFT calculations. J. Phys. Chem. A 104 (2000) 5475-5483
2. Emmeluth C., Dyczmons V., Kinzel T., Botschwina P., Suhm M.A., and Yáñez M. Combined jet relaxation and quantum chemical study of the pairing preferences of ethanol. Phys. Chem. Chem. Phys. 7 (2005) 991-997
3. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, Oxford
4. Buchhold K., Reimann B., Djafari S., Barth H.-D., Brutschy B., Tarakeshwar P., and Kim K.S. Fluorobenzene and p-difluorobenzene microsolvated by methanol: An infrared spectroscopic and ab initio theoretical investigation. J. Chem. Phys. 112 (2000) 1844-1858
5. Maienfisch P., and Hall R.G. The importance of fluorine in the life science industry. Chimia 58 (2004) 93-99
6. 2 OH reaction between 238 and 355 K. Phys. Chem. Chem. Phys. 7 (2005) 2498-2505
7. Buckley P., Giguère P.A., and Yamamoto D. Infrared studies on rotational isomerism. II. 2-Fluoroethanol. Can. J. Chem. 46 (1968) 2917-2923
8. Radom L., Lathan W.A., Hehre W.J., and Pople J.A. Molecular orbital theory of the electronic structure of organic compounds. XVII. Internal rotation in 1,2-disubtituded ethanes. J. Am. Chem. Soc. 95 (1972) 693-698
9. Huang J., and Hedberg K. Conformational analysis. 13. 2-Fluoroethanol. An investigation of the molecular structure and conformational composition at 20, 156, and 240 °C. Estimate of the anti-gauche energy difference. J. Am. Chem. Soc. 111 (1989) 6909-6913
10. Dixon D.A., and Smart B.E. Conformational energies of 2-fluoroethanol and 2-fluoroacetaldehyde enol: strength of the internal hydrogen bond. J. Phys. Chem. 95 (1991) 1609-1612
11. Buemi G. Molecular conformations and rotation barriers of 2-halogeno ethanethiols and 2-halogenoethanols: an ab initio study. J. Chem. Soc. Faraday Trans. 90 (1994) 1211-1215
12. Bakke J.M., Bjerkeseth L.H., Rønnow T.E.C.L., and Steinsvoll K. The conformation of 2-fluoroethanol-is intramolecular hydrogen bonding important?. J. Mol. Struct. 321 (1994) 205-214
13. Durig J.R., Klaeboe P., Guirgis G.A., Wang L., and Liu J. Far infrared spectra, conformational equilibrium, barriers to internal rotation, vibrational assignment and ab initio calculations of 2-fluoroethanol. Z. Phys. Chem. 191 (1995) 23-45
14. Gounev T.K., Bell S., Zhou L., and Durig J.R. Conformational studies of 2-fluoroethanol in liquid xenon from temperature dependence FT-IR spectra. J. Mol. Struct. 447 (1998) 21-32
15. -1. J. Chem. Phys. 110 (1999) 1979-1989
16. Buckton K.S., and Azrak R.G. Microwave spectrum and intramolecular hydrogen bonding in 2-fluoroethanol. J. Chem. Phys. 52 (1970) 5652-5655
17. Perttila M., Murto J., Kivenen A., and Turunen K. Fluoroalcohols - XXV. Matrix IR spectrum and normal coordinate analysis of 2-fluoroethanol. Spectrochim. Acta Part A 34 (1978) 9-13
18. Frei H., and Pimentel G.C. Infrared induced photochemical processes in matrices. Ann. Rev. Phys. Chem. 36 (1985) 491-524
19. Pourcin J., Davidovics G., Bodot H., Abouaf-Marguin L., and Gauthier-Roy B. Induced conformational isomerization of 2-fluoroethanol by selective infrared irradiation in argon matrix. Chem. Phys. Lett. 74 (1980) 147-151
20. Davidovics G., Pourcin J., Monnier M., Verlaque P., Bodot H., Abouaf-Marguin L., and Gautheir-Roy B. Experimental and theoretical determination of fundamental vibrations of 2-haloethanols. Part 2. Trans conformer of 2-fluoroethanol. J. Mol. Struct. 116 (1984) 39-47
21. Shirk J.S., and Marquardt C.L. Vibrational selectivity in the single-photon infrared photochemistry of matrix-isolated 2-fluoroethanol. J. Chem. Phys. 92 (1990) 7234-7240
22. Häber T., Schmitt U., and Suhm M.A. FTIR-spectroscopy of molecular clusters in pulsed supersonic slit-jet expansions. Phys. Chem. Chem. Phys. 1 (1999) 5573-5582
23. Le Barbu K., Brenner V., Millié P., Lahmani F., and Zehnacker-Rentien A. An experimental and theoretical study of jet-cooled complexes of chiral molecules: the role of dispersive forces in chiral discrimination. J. Phys. Chem. A 102 (1998) 128-137
24. Giardini Guidoni A., Piccirillo S., Scuderi D., Satta M., Di Palma T.M., and Speranza M. Chirality and intermolecular forces: studies using R2PI experiments in supersonic beams. Phys. Chem. Chem. Phys. 2 (2000) 4139-4142
25. Al-Rabaa A.R., Bréhéret E., Lahmani F., and Zehnacker A. Enantiodifferentiation in jet-cooled Van der Waals complexes of chiral molecules. Chem. Phys. Lett. 237 (1995) 480-484
26. Borho N., and Suhm M.A. Glycidol dimer: anatomy of a molecular handshake. Phys. Chem. Chem. Phys. 4 (2002) 2721-2732
27. Le Barbu K., Lahmani F., and Zehnacker A. A spectroscopic study of chiral discrimination in jet-cooled Van der Waals complexes. In: Hicks J.M. (Ed). Chirality: Physical Chemistry (2002), ACS, Washington 225-240
28. 2O nanoparticles. Faraday Discuss. Chem. Soc. 118 (2001) 331-359 (+contributions to the discussion on pp. 53, 119, 174-175, 179-180, 304-309, 361-363, 367-370)
29. Zimmermann D., Häber T., Schaal H., and Suhm M.A. Hydrogen-bonded rings, chains and lassos: the case of tert-butyl alcohol clusters. Mol. Phys. 99 (2001) 413-426
30. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, Revision B.04, Gaussian Inc., Pittsburgh PA, 2003.
31. Herzberg G. Molecular Spectra and Molecular Structure. I. Spectra of Diatomic Molecules (1950), D. van Nostrand, Princeton, NJ
32. van den Kerkhof T., Bouwen A., Goovaerts E., Herrebout W.A., and van der Veken B.J. Raman spectroscopy of cryosolutions: the Van der Waals complex of dimethyl ether with fluoroform. Phys. Chem. Chem. Phys. 6 (2004) 358-362
33. Emilsson T., Germann T.C., and Gutowsky H.S. Kinetics of molecular association and relaxation in a pulsed supersonic expansion. J. Chem. Phys. 96 (1992) 8830-8839
34. Portmann S., Inauen A., Lüthi H.P., and Leutwyler S. Chiral discrimination in hydrogen-bonded complexes. J. Chem. Phys. 113 (2000) 9577-9585
35. Picazo O., Alkorta I., and Elguero J. Dimers of 1,8a-dihydro-1,8-naphthyridine derivatives as models of chiral self-recognition. Struct. Chem. 16 (2005) 339-345