JOURNAL ARTICLE

Unlocking a new hydrogen-bonding marker: C–O bond shortening in vicinal diols revealed by rotational spectroscopy.

  • Published In: Journal of Chemical Physics, 2024, v. 160, n. 15. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Ma, Jiarui; Insausti, Aran; Al-Jabiri, Mohamad H.; Carlson, Colton D.; Jäger, Wolfgang; Xu, Yunjie 3 of 3

Abstract

This article focuses on the conformational analysis and intramolecular hydrogen-bonding characteristics of cis-1,2-cyclohexanediol, a model cyclic vicinal diol, using jet-cooled chirped-pulse Fourier transform microwave (CP-FTMW) spectroscopy combined with density functional theory (DFT) calculations. Four low-energy conformers were computationally identified, with two experimentally observed, revealing a strong preference for hydrogen bonding where the axial hydroxyl group donates to the equatorial hydroxyl group. A key finding is the consistent shortening of the C–O bond length in the hydrogen-bond donor compared to the acceptor, proposed as a novel marker for intramolecular hydrogen bonding in vicinal diols and related polyols. These structural insights may aid in understanding and selectively manipulating C–OH bonds in organic synthesis involving vicinal diols.

Additional Information

  • Source:Journal of Chemical Physics. 2024/04, Vol. 160, Issue 15, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2024
  • ISSN:0021-9606
  • DOI:10.1063/5.0203123
  • Accession Number:176721019
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