On the competition between weak O-H•••F and C-H•••F hydrogen bonds, in cooperation with C-H•••O contacts, in the difluoromethane-tert-butyl alcohol cluster

被引：22
|
作者：
Spada, Lorenzo [1 ]
Tasinato, Nicola [1 ]
Bosi, Giulio [2 ]
Vazart, Fanny [1 ]
Barone, Vincenzo [1 ]
Puzzarini, Cristina [2 ]
机构：
[1] Scuola Normale Super Pisa, Piazza Cavalieri 7, I-56126 Pisa, Italy
[2] Univ Bologna, Dipartimento Chim G Ciamician, Via Selmi 2, I-40126 Bologna, Italy
来源：
JOURNAL OF MOLECULAR SPECTROSCOPY | 2017年 / 337卷
关键词：
Weak hydrogen bonds; Rotational spectroscopy; Quantum chemistry; DFT calculations; Non-covalent interactions; SILICA-BASED MATERIALS; ROTATIONAL SPECTRUM; BASIS-SETS; VIBRATIONAL PROPERTIES; WAVE-FUNCTIONS; GAS-PHASE; WATER; SPECTROSCOPY; FLUORINE; THERMODYNAMICS;
D O I：
10.1016/j.jms.2017.04.001
中图分类号：
O64 [物理化学（理论化学）、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号：
070203 ; 070304 ; 081704 ; 1406 ;
摘要：
The 1:1 complex of tert-butyl alcohol with difluoromethane has been characterized by means of a joint experimental-computational investigation. Its rotational spectrum has been recorded by using a pulsed jet Fourier-Transform microwave spectrometer. The experimental work has been guided and supported by accurate quantum-chemical calculations. In particular, the computed potential energy landscape pointed out the formation of three stable isomers. However, the very low interconversion barriers explain why only one isomer, showing one O-H center dot center dot center dot F and two C-H center dot center dot center dot O weak hydrogen bonds, has been experimentally characterized. The effect of the H tert-butyl-group substitution has been analyzed from the comparison to the difluoromethane-water adduct. (C) 2017 Elsevier Inc. All rights reserved.
引用
收藏
页码：90 / 95
页数：6
相关论文
共 50 条
  • [11] Electrooxidative Ruthenium-Catalyzed C-H/O-H Annulation by Weak O-Coordination
    Qiu, Youai
    Tian, Cong
    Massignan, Leonardo
    Rogge, Torben
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (20) : 5818 - 5822
  • [12] Are the Intramolecular O-H•••F and O-H•••Cl Hydrogen Bonds Maintained in Solution? A Theoretical Study
    Nagy, Peter I.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2013, 117 (13) : 2812 - 2826
  • [13] Proline C-H Bonds as Loci for Proline Assembly via C-H/O Interactions
    Daniecki, Noah J.
    Bhatt, Megh R.
    Yap, Glenn P. A.
    Zondlo, Neal J.
    CHEMBIOCHEM, 2022, 23 (24)
  • [14] Evaluation of C-H•••O hydrogen bonds in native and misfolded proteins
    Chamberlain, AK
    Bowie, JU
    JOURNAL OF MOLECULAR BIOLOGY, 2002, 322 (03) : 497 - 503
  • [15] Strong structuring arising from weak cooperative O-H•••π and C-H•••O hydrogen bonding in benzene-methanol solution
    DiMino, Camilla
    Seel, Andrew G.
    Clancy, Adamj.
    Headen, ThomasF.
    Foldes, Tamas
    Rosta, Edina
    Sella, Andrea
    Skipper, Neal T.
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [16] Probing Fluorine Interactions in a Polyhydroxylated Environment: Conservation of a C-F•••H-C Recognition Motif in Presence of O-H•••O Hydrogen Bonds
    Mehta, Goverdhan
    Sen, Saikat
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (18) : 3387 - 3394
  • [17] Probing the C-H Weak Hydrogen Bond in Anesthetic Binding: The Sevoflurane-Benzene Cluster
    Seifert, Nathan A.
    Zaleski, Daniel P.
    Perez, Cristobal
    Neill, Justin L.
    Pate, Brooks H.
    Vallejo-Lopez, Montserrat
    Lesarri, Alberto
    Cocinero, Emilio J.
    Castano, Fernando
    Kleiner, Isabelle
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (12) : 3210 - 3213
  • [18] Impact of Intramolecular Hydrogen Bonding on the Reactivity of Cupric Superoxide Complexes with O-H and C-H Substrates
    Diaz, Daniel E.
    Quist, David A.
    Herzog, Austin E.
    Schaefer, Andrew W.
    Kipouros, Ioannis
    Bhadra, Mayukh
    Solomon, Edward, I
    Karlin, Kenneth D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) : 17572 - 17576
  • [19] Influence of C-H•••O Hydrogen Bonds on Macroscopic Properties of Supramolecular Assembly
    Ji, Wei
    Liu, Guofeng
    Li, Zijian
    Feng, Chuanliang
    ACS APPLIED MATERIALS & INTERFACES, 2016, 8 (08) : 5188 - 5195
  • [20] Molybdenum Carbide: Controlling the Geometric and Electronic Structure of Noble Metals for the Activation of O-H and C-H Bonds
    Deng, Yuchen
    Ge, Yuzhen
    Xu, Ming
    Yu, Qiaolin
    Xiao, Dequan
    Yao, Siyu
    Ma, Ding
    ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (12) : 3372 - 3383
12345