The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy

Research output: Contribution to journal › Article › Research › peer review

Authors

  • Juan Wang
  • Lorenzo Spada
  • Junhua Chen
  • Shuang Gao
  • Silvia Alessandrini
  • Gang Feng
  • Cristina Puzzarini
  • Qian Gou
  • Jens-Uwe Grabow
  • Vincenzo Barone

Research Organisations

External Research Organisations

  • Chongqing University
  • University of Bologna
  • Scuola Normale Superiore di Pisa
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Details

Original languageEnglish
Pages (from-to)13935-13941
Number of pages7
JournalAngewandte Chemie
Volume58
Issue number39
Early online date30 Jul 2019
Publication statusPublished - 24 Sept 2019

Abstract

Accurate quantum-chemical computations, combined with SAPT and NBO analyses, unveiled the intermolecular interactions occurring in cycloalkene–water, CnH2n−2–H2O (n=3–7), adducts, thus pointing out the dominant O−H⋅⋅⋅πC=C hydrogen bond. For n≥5, the members of this series show very similar intermolecular interactions and dissociation energies, with the primary contact being also assisted by a weaker C−H⋅⋅⋅O hydrogen bond. Based on this consideration, the cyclopentene–water complex was subsequently fully characterized by combining rotational spectroscopy in supersonic expansion with the capability of state-of-the-art quantum-chemical computations in accurately determining structural and energetic properties. The assignment of the rotational spectra for four isotopologues allowed the determination of an accurate semi-experimental equilibrium structure for the heavy-atom backbone of the molecular adduct.

Keywords

    bond analysis, microsolvation, noncovalent interactions, quantum chemistry, rotational spectroscopy

ASJC Scopus subject areas

Cite this

The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy. / Wang, Juan; Spada, Lorenzo; Chen, Junhua et al.
In: Angewandte Chemie , Vol. 58, No. 39, 24.09.2019, p. 13935-13941.

Research output: Contribution to journal › Article › Research › peer review

Wang, J, Spada, L, Chen, J, Gao, S, Alessandrini, S, Feng, G, Puzzarini, C, Gou, Q, Grabow, J-U & Barone, V 2019, 'The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy', Angewandte Chemie , vol. 58, no. 39, pp. 13935-13941. https://doi.org/10.1002/anie.201906977
Wang, J., Spada, L., Chen, J., Gao, S., Alessandrini, S., Feng, G., Puzzarini, C., Gou, Q., Grabow, J.-U., & Barone, V. (2019). The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy. Angewandte Chemie , 58(39), 13935-13941. https://doi.org/10.1002/anie.201906977
Wang J, Spada L, Chen J, Gao S, Alessandrini S, Feng G et al. The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy. Angewandte Chemie . 2019 Sept 24;58(39):13935-13941. Epub 2019 Jul 30. doi: 10.1002/anie.201906977
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title = "The Unexplored World of Cycloalkene–Water Complexes: Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy",
abstract = "Accurate quantum-chemical computations, combined with SAPT and NBO analyses, unveiled the intermolecular interactions occurring in cycloalkene–water, CnH2n−2–H2O (n=3–7), adducts, thus pointing out the dominant O−H⋅⋅⋅πC=C hydrogen bond. For n≥5, the members of this series show very similar intermolecular interactions and dissociation energies, with the primary contact being also assisted by a weaker C−H⋅⋅⋅O hydrogen bond. Based on this consideration, the cyclopentene–water complex was subsequently fully characterized by combining rotational spectroscopy in supersonic expansion with the capability of state-of-the-art quantum-chemical computations in accurately determining structural and energetic properties. The assignment of the rotational spectra for four isotopologues allowed the determination of an accurate semi-experimental equilibrium structure for the heavy-atom backbone of the molecular adduct.",
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author = "Juan Wang and Lorenzo Spada and Junhua Chen and Shuang Gao and Silvia Alessandrini and Gang Feng and Cristina Puzzarini and Qian Gou and Jens-Uwe Grabow and Vincenzo Barone",
note = "Funding Information: We are grateful for support from the National Natural Science Foundation of China (Grant No. 21703021), the Fundamental and Frontier Research Fund of Chongqing (Grant No. cstc2017jcyjAX0068 and No. cstc2018jcyjAX0050), the Venture & Innovation Support Program for Chongqing Overseas Returns (Grant No. cx2018064), the Foundation of 100 Young Chongqing University (Grant No. 0220001104428), and the Fundamental Research Funds for the Central Universities (Grant No. 106112017CDJQJ228807 and 2018CDQYHG0009). J.W. thanks the China Scholarships Council (CSC) for financial support. Support from the Land Niedersachsen and the Deutsche Forschungsgemeinschaft (DFG) is acknowledged for the work carried out in Hannover. In Bologna, this study has been supported by the University of Bologna (RFO funds). In Pisa, this study has been supported by funding and computational resources of the SMART Laboratory of the Scuola Normale Superiore.",
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T1 - The Unexplored World of Cycloalkene–Water Complexes

T2 - Primary and Assisting Interactions Unraveled by Experimental and Computational Spectroscopy

AU - Wang, Juan

AU - Spada, Lorenzo

AU - Chen, Junhua

AU - Gao, Shuang

AU - Alessandrini, Silvia

AU - Feng, Gang

AU - Puzzarini, Cristina

AU - Gou, Qian

AU - Grabow, Jens-Uwe

AU - Barone, Vincenzo

N1 - Funding Information: We are grateful for support from the National Natural Science Foundation of China (Grant No. 21703021), the Fundamental and Frontier Research Fund of Chongqing (Grant No. cstc2017jcyjAX0068 and No. cstc2018jcyjAX0050), the Venture & Innovation Support Program for Chongqing Overseas Returns (Grant No. cx2018064), the Foundation of 100 Young Chongqing University (Grant No. 0220001104428), and the Fundamental Research Funds for the Central Universities (Grant No. 106112017CDJQJ228807 and 2018CDQYHG0009). J.W. thanks the China Scholarships Council (CSC) for financial support. Support from the Land Niedersachsen and the Deutsche Forschungsgemeinschaft (DFG) is acknowledged for the work carried out in Hannover. In Bologna, this study has been supported by the University of Bologna (RFO funds). In Pisa, this study has been supported by funding and computational resources of the SMART Laboratory of the Scuola Normale Superiore.

PY - 2019/9/24

Y1 - 2019/9/24

N2 - Accurate quantum-chemical computations, combined with SAPT and NBO analyses, unveiled the intermolecular interactions occurring in cycloalkene–water, CnH2n−2–H2O (n=3–7), adducts, thus pointing out the dominant O−H⋅⋅⋅πC=C hydrogen bond. For n≥5, the members of this series show very similar intermolecular interactions and dissociation energies, with the primary contact being also assisted by a weaker C−H⋅⋅⋅O hydrogen bond. Based on this consideration, the cyclopentene–water complex was subsequently fully characterized by combining rotational spectroscopy in supersonic expansion with the capability of state-of-the-art quantum-chemical computations in accurately determining structural and energetic properties. The assignment of the rotational spectra for four isotopologues allowed the determination of an accurate semi-experimental equilibrium structure for the heavy-atom backbone of the molecular adduct.

AB - Accurate quantum-chemical computations, combined with SAPT and NBO analyses, unveiled the intermolecular interactions occurring in cycloalkene–water, CnH2n−2–H2O (n=3–7), adducts, thus pointing out the dominant O−H⋅⋅⋅πC=C hydrogen bond. For n≥5, the members of this series show very similar intermolecular interactions and dissociation energies, with the primary contact being also assisted by a weaker C−H⋅⋅⋅O hydrogen bond. Based on this consideration, the cyclopentene–water complex was subsequently fully characterized by combining rotational spectroscopy in supersonic expansion with the capability of state-of-the-art quantum-chemical computations in accurately determining structural and energetic properties. The assignment of the rotational spectra for four isotopologues allowed the determination of an accurate semi-experimental equilibrium structure for the heavy-atom backbone of the molecular adduct.

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KW - noncovalent interactions

KW - quantum chemistry

KW - rotational spectroscopy

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