ACS Publications. Most Trusted. Most Cited. Most Read
Hydrogen Bonding in 2-Propanol. The Effect of Fluorination
My Activity

Figure 1Loading Img
    Article

    Hydrogen Bonding in 2-Propanol. The Effect of Fluorination
    Click to copy article linkArticle link copied!

    View Author Information
    Institut für Physikalische Chemie, Universität Göttingen, Tammannstrasse 6, 37077 Göttingen, Germany
    Other Access Options

    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2000, 104, 2, 265–274
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp9928558
    Published December 16, 1999
    Copyright © 2000 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!

    Fourier transform infrared (FTIR) spectra at thermal equilibrium and in seeded, pulsed slit jet expansions of 2-propanol (IP), 1,1,1-trifluoro-2-propanol (TFIP), and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) reveal dimers, oligomers, and large clusters as well as conformational isomerism of the monomers. The assignments are supported by hybrid density functional calculations. The effect of methyl group fluorination on OH frequency shift and intensity enhancement, torsional energetics, hydrogen bond strength, and cluster stability trends is investigated. HFIP promises to be a valuable prototype for spectroscopic studies of intramolecular torsional isomerization dynamics (as already shown in Quack, M. Faraday Discuss. Chem. Soc.1995, 102, 104−107) and its coupling to intermolecular hydrogen bonding.

    Copyright © 2000 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

     Dedicated to Prof. Dr. W. Lüttke on the occasion of his 80th birthday.

    *

     Corresponding author. E-mail:  [email protected]/FAX:  +49 551 393117.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 84 publications.

    1. Hanliang Zheng, Liu Cai, Xiaoyu Lai, Muhammet Uyanik, Kazuaki Ishihara, Xiao-Song Xue. Unraveling Alcohol Additive Effects on Hypervalent Iodine(III)-Catalyzed Asymmetric Phenolic Dearomatization: Ligand Substitution and Low-Barrier Hydrogen Bonds. ACS Catalysis 2025, 15 (1) , 370-380. https://doi.org/10.1021/acscatal.4c06557
    2. Casper Vindahl Jensen, Emil Vogt, Andras Sun Poulsen, Henrik G. Kjaergaard. Room Temperature Gas Phase Equilibrium Constants of the Methanol Dimer, Trimer, and Tetramer. The Journal of Physical Chemistry A 2024, 128 (31) , 6382-6391. https://doi.org/10.1021/acs.jpca.4c02730
    3. Nozomi Yoneda, Haruka Iyama, Takashi Nagata, Masato Katahira, Yoshiki Ishii, Kohei Tada, Kazuhiko Matsumoto, Rika Hagiwara. Fluoride Ion in Alcohols: Isopropanol vs Hexafluoroisopropanol. The Journal of Physical Chemistry Letters 2024, 15 (6) , 1677-1685. https://doi.org/10.1021/acs.jpclett.3c03619
    4. Heonjae Jeong, Ethan P. Kamphaus, Paul C. Redfern, Nathan T. Hahn, Noel J. Leon, Chen Liao, Lei Cheng. Computational Predictions of the Stability of Fluorinated Calcium Aluminate and Borate Salts. ACS Applied Materials & Interfaces 2023, 15 (5) , 6933-6941. https://doi.org/10.1021/acsami.2c20661
    5. Bowei Wu, Arsh S. Hazrah, Nathan A. Seifert, Sönke Oswald, Wolfgang Jäger, Yunjie Xu. Higher-Energy Hexafluoroisopropanol···Water Isomer and Its Large Amplitude Motions: Rotational Spectra and DFT Calculations. The Journal of Physical Chemistry A 2021, 125 (48) , 10401-10409. https://doi.org/10.1021/acs.jpca.1c09058
    6. Bowei Wu, Nathan A. Seifert, Sönke Oswald, Wolfgang Jäger, Yunjie Xu. Rotational Spectrum and Molecular Structures of the Binary Aggregates of 1,1,1,3,3,3-Hexafluoro-2-propanol with Ne and Ar. The Journal of Physical Chemistry A 2021, 125 (24) , 5355-5364. https://doi.org/10.1021/acs.jpca.1c03757
    7. Abhishek Shahi and Elangannan Arunan . Microwave Spectrum of Hexafluoroisopropanol and Torsional Behavior of Molecules with a CF3–C–CF3 Group. The Journal of Physical Chemistry A 2015, 119 (22) , 5650-5657. https://doi.org/10.1021/acs.jpca.5b03240
    8. Albrecht Berkessel, Sonja S. Vormittag, Nils E. Schlörer, and Jörg-M. Neudörfl . TEFDDOLs (α,α,α′,α′-Tetrakis(perfluoroaryl/alkyl)-2,2′-dimethyl-1,3-dioxolane-4,5-dimethanols): Highly Fluorinated Chiral H-Bond Donors and Brønsted Acids with Distinct H-Bonding Patterns and Supramolecular Architectures. The Journal of Organic Chemistry 2012, 77 (22) , 10145-10157. https://doi.org/10.1021/jo301609g
    9. Qiang Tang, Xingkuan Chen, Bhoopendra Tiwari, and Yonggui Robin Chi . Addition of Indoles to Oxyallyl Cations for Facile Access to α-Indole Carbonyl Compounds. Organic Letters 2012, 14 (7) , 1922-1925. https://doi.org/10.1021/ol300591z
    10. Luca Evangelisti, Galen Sedo, and Jennifer van Wijngaarden . Rotational Spectrum of 1,1,1-Trifluoro-2-butanone Using Chirped-Pulse Fourier Transform Microwave Spectroscopy. The Journal of Physical Chemistry A 2011, 115 (5) , 685-690. https://doi.org/10.1021/jp1089905
    11. Marco Colladon,, Alessandro Scarso,, Paolo Sgarbossa,, Rino A. Michelin, and, Giorgio Strukul. Regioselectivity and Diasteroselectivity in Pt(II)-Mediated “Green” Catalytic Epoxidation of Terminal Alkenes with Hydrogen Peroxide:  Mechanistic Insight into a Peculiar Substrate Selectivity. Journal of the American Chemical Society 2007, 129 (24) , 7680-7689. https://doi.org/10.1021/ja071142x
    12. Christine Cézard,, Corey A. Rice, and, Martin A. Suhm. OH-Stretching Red Shifts in Bulky Hydrogen-Bonded Alcohols:  Jet Spectroscopy and Modeling. The Journal of Physical Chemistry A 2006, 110 (32) , 9839-9848. https://doi.org/10.1021/jp0610362
    13. Albrecht Berkessel,, Jens A. Adrio,, Daniel Hüttenhain, and, Jörg M. Neudörfl. Unveiling the “Booster Effect” of Fluorinated Alcohol Solvents:  Aggregation-Induced Conformational Changes and Cooperatively Enhanced H-Bonding. Journal of the American Chemical Society 2006, 128 (26) , 8421-8426. https://doi.org/10.1021/ja0545463
    14. Maia Sokolova,, Stephen J. Barlow,, Galina V. Bondarenko,, Yuri E. Gorbaty, and, Martyn Poliakoff. Comparison between IR Absorption and Raman Scattering Spectra of Liquid and Supercritical 1-Butanol. The Journal of Physical Chemistry A 2006, 110 (11) , 3882-3885. https://doi.org/10.1021/jp055931h
    15. Harald Møllendal. Structural and Conformational Properties of 1,1,1-Trifluoro-2-propanol Investigated by Microwave Spectroscopy and Quantum Chemical Calculations. The Journal of Physical Chemistry A 2005, 109 (42) , 9488-9493. https://doi.org/10.1021/jp052905a
    16. John M. Stubbs and, J. Ilja Siepmann. Elucidating the Vibrational Spectra of Hydrogen-Bonded Aggregates in Solution:  Electronic Structure Calculations with Implicit Solvent and First-Principles Molecular Dynamics Simulations with Explicit Solvent for 1-Hexanol in n-Hexane. Journal of the American Chemical Society 2005, 127 (13) , 4722-4729. https://doi.org/10.1021/ja044380q
    17. Yu. B. Vysotsky,, V. S. Bryantsev,, F. L. Boldyreva,, V. B. Fainerman, and, D. Vollhardt. Quantum Chemical Semiempirical Approach to the Structural and Thermodynamic Characteristics of Fluoroalkanols at the Air/Water Interface. The Journal of Physical Chemistry B 2005, 109 (1) , 454-462. https://doi.org/10.1021/jp048240e
    18. Trevor Hoskins,, Won Jae Chung,, Ankur Agrawal,, Peter J. Ludovice, and, Clifford L. Henderson, , Larry D. Seger,, Larry F. Rhodes, and, Robert A. Shick. Bis(trifluoromethyl)carbinol-Substituted Polynorbornenes:  Dissolution Behavior. Macromolecules 2004, 37 (12) , 4512-4518. https://doi.org/10.1021/ma0347417
    19. Volker Dyczmons. Dimers of Ethanol. The Journal of Physical Chemistry A 2004, 108 (11) , 2080-2086. https://doi.org/10.1021/jp030930f
    20. Nakul C. Maiti,, Paul R. Carey, and, Vernon E. Anderson. Correlation of an Alcohol's αC−D Stretch with Hydrogen Bond Strength in Complexes with Amines. The Journal of Physical Chemistry A 2003, 107 (46) , 9910-9917. https://doi.org/10.1021/jp0349334
    21. Marco Fioroni,, Klaus Burger,, Alan E. Mark, and, Danilo Roccatano. The Influence of Trifluoromethyl Groups on the Miscibility of Fluorinated Alcohols with Water:  A Molecular Dynamics Simulation Study of 1,1,1-Trifluoropropan-2-ol in Aqueous Solution. The Journal of Physical Chemistry B 2003, 107 (20) , 4855-4861. https://doi.org/10.1021/jp026076u
    22. Stephen J. Barlow,, Galina V. Bondarenko,, Yuri E. Gorbaty,, Toshio Yamaguchi, and, Martyn Poliakoff . An IR Study of Hydrogen Bonding in Liquid and Supercritical Alcohols. The Journal of Physical Chemistry A 2002, 106 (43) , 10452-10460. https://doi.org/10.1021/jp0135095
    23. John M. Stubbs and, J. Ilja Siepmann. Aggregation in Dilute Solutions of 1-Hexanol in n-Hexane:  A Monte Carlo Simulation Study. The Journal of Physical Chemistry B 2002, 106 (15) , 3968-3978. https://doi.org/10.1021/jp013759l
    24. Marco Fioroni,, Klaus Burger,, Alan E. Mark, and, Danilo Roccatano. Model of 1,1,1,3,3,3-Hexafluoro-propan-2-ol for Molecular Dynamics Simulations. The Journal of Physical Chemistry B 2001, 105 (44) , 10967-10975. https://doi.org/10.1021/jp012476q
    25. Seyed Foad Aghamiri,, Hamid Modarress, and, G. Ali Mansoori. A New Theoretical Approach to the Hydrogen-Bonded Fluids Based on the Conformal Solution Concept. The Journal of Physical Chemistry B 2001, 105 (14) , 2820-2825. https://doi.org/10.1021/jp003268l
    26. Milena Barp, Florian Kreuter, Qian-Rui Huang, Jiaye Jin, Franka. E. Ninov, Jer-Lai Kuo, Ralf Tonner-Zech, Knut R. Asmis. Quantifying hexafluoroisopropanol's hydrogen bond donor ability: infrared photodissociation spectroscopy of halide anion HFIP complexes. Chemical Science 2025, 16 (12) , 5174-5185. https://doi.org/10.1039/D4SC08456J
    27. Federico Caporaletti, Lucas Gunkel, M. Ángeles Fernández‐Ibáñezhttps, Johannes Hunger, Sander Woutersen. Schnelle kollektive Wasserstoffbrückenbindungsdynamik in Hexafluorisopropanol im Kontext seiner chemischen Aktivität. Angewandte Chemie 2024, 136 (52) https://doi.org/10.1002/ange.202416091
    28. Federico Caporaletti, Lucas Gunkel, M. Ángeles Fernández‐Ibáñez, Johannes Hunger, Sander Woutersen. Fast Collective Hydrogen‐Bond Dynamics in Hexafluoroisopropanol Related to its Chemical Activity. Angewandte Chemie International Edition 2024, 63 (52) https://doi.org/10.1002/anie.202416091
    29. Beppo Hartwig, Melanie Schnell, Martin A. Suhm, Daniel A. Obenchain. Weak hydrogen bonding to halogens and chirality communication in propanols: Raman and microwave spectroscopy benchmark theory. Physical Chemistry Chemical Physics 2024, 26 (12) , 9432-9452. https://doi.org/10.1039/D3CP04911F
    30. N. Shabani, M. R. Poor Heravi, M. Babazadeh, E. Ghasemi, M. Amini, C. Robertson. Green Synthesis of 2H-Pyrano[2,3-d][1,3]thiazole-6-carbonitriles in Trifluoroethanol as an Efficient Acidic Solvent and Their Biological Activity. Russian Journal of Organic Chemistry 2024, 60 (1) , 115-124. https://doi.org/10.1134/S1070428024010159
    31. Iker León, Alberto Lesarri, José A. Fernández. Noncovalent interactions in isolated molecular aggregates: From single molecules to nanostructures. 2021, 143-188. https://doi.org/10.1016/B978-0-12-817586-6.00005-0
    32. Gwydyon Marchelli, J. Ingenmey, B. Kirchner. Activity coefficients of binary methanol alcohol mixtures from cluster weighting. ChemistryOpen 2020, 9 (7) , 774-785. https://doi.org/10.1002/open.202000171
    33. Jia Wang, Lanhai He, Jovana Petrovic, Ahmed Al-Refaie, Helen Bieker, Jolijn Onvlee, Karol Długołęcki, Jochen Küpper. Spatial separation of 2-propanol monomer and its ionization-fragmentation pathways. Journal of Molecular Structure 2020, 1208 , 127863. https://doi.org/10.1016/j.molstruc.2020.127863
    34. Sönke Oswald, Nathan A. Seifert, Fabian Bohle, Maxim Gawrilow, Stefan Grimme, Wolfgang Jäger, Yunjie Xu, Martin A. Suhm. The Chiral Trimer and a Metastable Chiral Dimer of Achiral Hexafluoroisopropanol: A Multi‐Messenger Study. Angewandte Chemie 2019, 131 (15) , 5134-5138. https://doi.org/10.1002/ange.201813881
    35. Sönke Oswald, Nathan A. Seifert, Fabian Bohle, Maxim Gawrilow, Stefan Grimme, Wolfgang Jäger, Yunjie Xu, Martin A. Suhm. The Chiral Trimer and a Metastable Chiral Dimer of Achiral Hexafluoroisopropanol: A Multi‐Messenger Study. Angewandte Chemie International Edition 2019, 58 (15) , 5080-5084. https://doi.org/10.1002/anie.201813881
    36. Takashi Doi, Tsutomu Shimokawa, Atsushi Sudo, Takeshi Endo. Fundamental investigation on interaction between hexafluoroisopropylalcohol‐containing styrene and photochemical acid generator for rationale design of photoresist system. Journal of Polymer Science Part A: Polymer Chemistry 2019, 57 (4) , 531-538. https://doi.org/10.1002/pola.29291
    37. Mykyta Iazykov, Moisés Canle, J. Arturo Santaballa, Ludmila Rublova. Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur. Journal of Physical Organic Chemistry 2018, 31 (2) https://doi.org/10.1002/poc.3753
    38. Paul J. Godin, Karine Le Bris, Kimberly Strong. Conformational analysis and global warming potentials of 1,1,1,3,3,3-hexafluoro-2-propanol from absorption spectroscopy. Journal of Quantitative Spectroscopy and Radiative Transfer 2017, 203 , 522-529. https://doi.org/10.1016/j.jqsrt.2017.04.031
    39. Sönke Oswald, Martin A. Suhm. Experimental Reference Data for Hexafluorinated Propanol by Exploring an Unusual Intermolecular Torsional Balance. Angewandte Chemie 2017, 129 (41) , 12846-12850. https://doi.org/10.1002/ange.201705301
    40. Sönke Oswald, Martin A. Suhm. Experimental Reference Data for Hexafluorinated Propanol by Exploring an Unusual Intermolecular Torsional Balance. Angewandte Chemie International Edition 2017, 56 (41) , 12672-12676. https://doi.org/10.1002/anie.201705301
    41. Saptarsi Mondal, Biswajit Biswas, Sunipa Sarkar, Prashant Chandra Singh. A combined molecular dynamics simulation, atoms in molecule analysis and IR study on the biologically important bulk fluorinated ethanols to understand the role of weak interactions in their cluster formation and hydrogen bond network. Journal of Molecular Liquids 2017, 240 , 708-716. https://doi.org/10.1016/j.molliq.2017.05.098
    42. Gregor Lipinski, Bert Mallik, Klaus Merz. In situ Crystallization Technique - an Approach to Circumvent Crystal Structures with high Z′-Crystallization Behavior of (CF 3 ) 2 C-OH. Zeitschrift für anorganische und allgemeine Chemie 2017, 643 (11) , 683-688. https://doi.org/10.1002/zaac.201700050
    43. Huaqi Zhan, Yongjun Hu, Pengchao Wang, Jiaxin Chen. Dominant conformer of tetrahydropyran-2-methanol and its clusters in the gas phase explored by the use of VUV photoionization and vibrational spectroscopy. The Journal of Chemical Physics 2017, 146 (13) https://doi.org/10.1063/1.4979298
    44. Bogdan Dereka, Eric Vauthey. Direct local solvent probing by transient infrared spectroscopy reveals the mechanism of hydrogen-bond induced nonradiative deactivation. Chemical Science 2017, 8 (7) , 5057-5066. https://doi.org/10.1039/C7SC00437K
    45. Khushbu Kushwaha, Balazs Pinter, Syeda A. Shehzadi, Chandi C. Malakar, Christophe M. L. Vande Velde, Frank de Proft, Kourosch Abbaspour Tehrani. Metal‐Free Synthesis of Chlorinated β‐Amino Ketones via an Unexpected Reaction of Imines with Arylacetylenes in 1,1,1,3,3,3‐Hexafluoro‐2‐propanol. Advanced Synthesis & Catalysis 2016, 358 (1) , 41-49. https://doi.org/10.1002/adsc.201500519
    46. A. Shahi, E. Arunan. Microwave spectroscopic and theoretical investigations of the strongly hydrogen bonded hexafluoroisopropanol⋯water complex. Physical Chemistry Chemical Physics 2015, 17 (38) , 24774-24782. https://doi.org/10.1039/C5CP03585F
    47. Yuanqin Yu, Yuxi Wang, Naiyin Hu, Ke Lin, Xiaoguo Zhou, Shilin Liu. Overlapping spectral features and new assignment of 2‐propanol in the C–H stretching region. Journal of Raman Spectroscopy 2014, 45 (3) , 259-265. https://doi.org/10.1002/jrs.4446
    48. Juan Luo, Hui Zhou, Jiwei Hu, Rui Wang, Qiang Tang. Efficient catalytic-free method to produce α-aryl cycloalkanones through highly chemoselective coupling of aryl compounds with oxyallyl cations. RSC Adv. 2014, 4 (33) , 17370-17377. https://doi.org/10.1039/C4RA01043D
    49. Ramprasad Misra, D.K. Maity, S.P. Bhattacharyya. Deciphering the role of multiple hydrogen bonding sites on the microsolvation of 3-(phenylamino)-2-cyclohexen-1-one with water in the excited states. Chemical Physics 2013, 425 , 148-155. https://doi.org/10.1016/j.chemphys.2013.09.001
    50. Jonas Altnöder, Aude Bouchet, Juhyon J. Lee, Katharina E. Otto, Martin A. Suhm, Anne Zehnacker-Rentien. Chirality-dependent balance between hydrogen bonding and London dispersion in isolated (±)-1-indanol clusters. Physical Chemistry Chemical Physics 2013, 15 (25) , 10167. https://doi.org/10.1039/c3cp50708d
    51. M. A. Suhm, F. Kollipost. Femtisecond single-mole infrared spectroscopy of molecular clusters. Physical Chemistry Chemical Physics 2013, 15 (26) , 10702. https://doi.org/10.1039/c3cp51515j
    52. P. Golub, V. Pogorelov, I. Doroshenko. The structural peculiarities of liquid n-heptanol and n-octanol. Journal of Molecular Liquids 2012, 169 , 80-86. https://doi.org/10.1016/j.molliq.2012.02.016
    53. Roman M. Balabin. Conformational equilibrium in alanine: Focal-point analysis and ab initio limit. Computational and Theoretical Chemistry 2011, 965 (1) , 15-21. https://doi.org/10.1016/j.comptc.2011.01.008
    54. Albrecht Berkessel. Catalytic Oxidations with Hydrogen Peroxide in Fluorinated Alcohol Solvents. 2010, 117-145. https://doi.org/10.1002/9783527632039.ch4
    55. Juhyon J. Lee, Susanne Hesse, Martin A. Suhm. Conformational instability upon dimerization: Prolinol. Journal of Molecular Structure 2010, 976 (1-3) , 397-404. https://doi.org/10.1016/j.molstruc.2010.03.052
    56. Joong-Won Shin, Elliot R. Bernstein. Experimental and theoretical studies of isolated neutral and ionic 2-propanol and their clusters. The Journal of Chemical Physics 2009, 130 (21) https://doi.org/10.1063/1.3148378
    57. Martin A. Suhm. Hydrogen Bond Dynamics in Alcohol Clusters. 2009, 1-57. https://doi.org/10.1002/9780470475935.ch1
    58. Huipeng Chen, Zhen Liu, Peggy Cebe. Chain confinement in electrospun nanofibers of PET with carbon nanotubes. Polymer 2009, 50 (3) , 872-880. https://doi.org/10.1016/j.polymer.2008.12.030
    59. Heiko Jacobsen. Fluorine substituent effects on dihydrogen bonding of transition metal hydrides. Physical Chemistry Chemical Physics 2009, 11 (33) , 7231. https://doi.org/10.1039/b900287a
    60. Izabela Franssen Szydłowska, Yevgeniy Nosenko, Bernhard Brutschy, Jerzy Herbich. Dual fluorescence of 4-dialkylaminopyridines under supersonic jet conditions. Chemical Physics Letters 2008, 467 (1-3) , 58-65. https://doi.org/10.1016/j.cplett.2008.11.027
    61. . Vibrational Analysis and Intermolecular Hydrogen Bonding of Azodicarbonamide in the Pentamer Cluster. Bulletin of the Korean Chemical Society 2008, 1951-1959. https://doi.org/10.5012/bkcs.2008.29.10.1951
    62. Anne Zehnacker, Martin A. Suhm. Chiralitätserkennung zwischen neutralen Molekülen in der Gasphase. Angewandte Chemie 2008, 120 (37) , 7076-7100. https://doi.org/10.1002/ange.200800957
    63. Anne Zehnacker, Martin A. Suhm. Chirality Recognition between Neutral Molecules in the Gas Phase. Angewandte Chemie International Edition 2008, 47 (37) , 6970-6992. https://doi.org/10.1002/anie.200800957
    64. Tina Scharge, Tobias N. Wassermann, Martin A. Suhm. Weak Hydrogen Bonds Make a Difference: Dimers of Jet-Cooled Halogenated Ethanols. Zeitschrift für Physikalische Chemie 2008, 222 (8-9) , 1407-1452. https://doi.org/10.1524/zpch.2008.5420
    65. Bogusława Czarnik-Matusewicz, Sylwia Pilorz, Dariusz Bieńko, Danuta Michalska. Molecular and electronic structures, infrared spectra, and vibrational assignment for ap and sc conformers of hexafluoro-iso-propanol. Vibrational Spectroscopy 2008, 47 (1) , 44-52. https://doi.org/10.1016/j.vibspec.2008.01.016
    66. T. N. Wassermann, C. A. Rice, M. A. Suhm, D. Luckhaus. Hydrogen bonding lights up overtones in pyrazoles. The Journal of Chemical Physics 2007, 127 (23) https://doi.org/10.1063/1.2806181
    67. Michael Hippler. Quantum chemical study and infrared spectroscopy of hydrogen-bonded CHCl3–NH3 in the gas phase. The Journal of Chemical Physics 2007, 127 (8) https://doi.org/10.1063/1.2757176
    68. J.-F. Berrien, M. Ourévitch, G. Morgant, N.E. Ghermani, B. Crousse, D. Bonnet-Delpon. A crystalline H-bond cluster of hexafluoroisopropanol (HFIP) and piperidine. Journal of Fluorine Chemistry 2007, 128 (7) , 839-843. https://doi.org/10.1016/j.jfluchem.2007.03.014
    69. Liping Zhang, Isao Noda, Boguslawa Czarnik-Matusewicz, Yuqing Wu. Multivariate Estimation between Mid and Near-Infrared Spectra of Hexafluoroisopropanol-Water Mixtures. Analytical Sciences 2007, 23 (7) , 901-905. https://doi.org/10.2116/analsci.23.901
    70. R. Wugt Larsen, Philipp Zielke, Martin A. Suhm. Hydrogen-bonded OH stretching modes of methanol clusters: A combined IR and Raman isotopomer study. The Journal of Chemical Physics 2007, 126 (19) https://doi.org/10.1063/1.2732745
    71. Tina Scharge, Christine Cézard, Philipp Zielke, Anne Schütz, Corinna Emmeluth, Martin A. Suhm. A peptide co-solvent under scrutiny: self-aggregation of 2,2,2-trifluoroethanol. Physical Chemistry Chemical Physics 2007, 9 (32) , 4472. https://doi.org/10.1039/b705498j
    72. Izabela Szydłowska, Yevgeniy Nosenko, Bernhard Brutschy, P. Tarakeshwar, Jerzy Herbich. Supersonic jet studies of solvation effects on the spectroscopy and photophysics of 4-diethylaminopyridine. Physical Chemistry Chemical Physics 2007, 9 (36) , 4981. https://doi.org/10.1039/b705532c
    73. Kevin O. Douglass, James E. Johns, Pradeep M. Nair, Gordon G. Brown, Frances S. Rees, Brooks H. Pate. Applications of Fourier transform microwave (FTMW) detected infrared–microwave double-resonance spectroscopy to problems in vibrational dynamics. Journal of Molecular Spectroscopy 2006, 239 (1) , 29-40. https://doi.org/10.1016/j.jms.2006.05.015
    74. Susan Chung, Michael Hippler. Infrared spectroscopy of hydrogen-bonded CHCl3–SO2 in the gas phase. The Journal of Chemical Physics 2006, 124 (21) https://doi.org/10.1063/1.2207617
    75. Tina Scharge, Thomas Häber, Martin A. Suhm. Quantitative chirality synchronization in trifluoroethanol dimers. Phys. Chem. Chem. Phys. 2006, 8 (40) , 4664-4667. https://doi.org/10.1039/B609868A
    76. María A. Muñoz, Manuel Galán, Carmen Carmona, Manuel Balón. Hydrogen-bonding interactions between 1-methylindole and alcohols. Chemical Physics Letters 2005, 401 (1-3) , 109-114. https://doi.org/10.1016/j.cplett.2004.10.156
    77. Corinna Emmeluth, Volker Dyczmons, Tom Kinzel, Peter Botschwina, Martin A. Suhm, Manuel Yáñez. Combined jet relaxation and quantum chemical study of the pairing preferences of ethanol. Phys. Chem. Chem. Phys. 2005, 7 (5) , 991-997. https://doi.org/10.1039/B417870J
    78. John M. Stubbs, J. Ilja Siepmann. Binary phase behavior and aggregation of dilute methanol in supercritical carbon dioxide: A Monte Carlo simulation study. The Journal of Chemical Physics 2004, 121 (3) , 1525-1534. https://doi.org/10.1063/1.1763842
    79. Albrecht Berkessel, Jens A. Adrio. Kinetic Studies of Olefin Epoxidation with Hydrogen Peroxide in 1,1,1,3,3,3‐Hexafluoro‐2‐propanol Reveal a Crucial Catalytic Role for Solvent Clusters. Advanced Synthesis & Catalysis 2004, 346 (2-3) , 275-280. https://doi.org/10.1002/adsc.200303222
    80. Michal Fárník, Christof Steinbach, Marcus Weimann, Udo Buck, Nicole Borho, Martin A. Suhm. Size-selective vibrational spectroscopy of methyl glycolate clusters: comparison with ragout-jet FTIR spectroscopy. Phys. Chem. Chem. Phys. 2004, 6 (19) , 4614-4620. https://doi.org/10.1039/B408506J
    81. M.A Muñoz, M Galán, L Gómez, C Carmona, P Guardado, M Balón. The pyrrole ring as hydrogen-bonding π-donor base: an experimental and theoretical study of the interactions of N-methylpyrrole with alcohols. Chemical Physics 2003, 290 (1) , 69-77. https://doi.org/10.1016/S0301-0104(03)00100-9
    82. Maria Vittoria Spanedda, Vu Dinh Hoang, Benoit Crousse, Danièle Bonnet-Delpon, Jean-Pierre Bégué. Aza-Diels–Alder reaction in fluorinated alcohols. A one-pot synthesis of tetrahydroquinolines. Tetrahedron Letters 2003, 44 (2) , 217-219. https://doi.org/10.1016/S0040-4039(02)02558-3
    83. Kalju Kahn, Thomas C. Bruice. Parameterization of OPLS–AA force field for the conformational analysis of macrocyclic polyketides. Journal of Computational Chemistry 2002, 23 (10) , 977-996. https://doi.org/10.1002/jcc.10051
    84. D. ZIMMERMANN, TH. HÄBER, H. SCHAAL, M. A. SUHM. Hydrogen bonded rings, chains and lassos: the case of t-butyl alcohol clusters. Molecular Physics 2001, 99 (5) , 413-425. https://doi.org/10.1080/00268970010017009

    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2000, 104, 2, 265–274
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp9928558
    Published December 16, 1999
    Copyright © 2000 American Chemical Society

    Article Views

    1270

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.