Evidence for intramolecular OH⋯π hydrogen bonding in unsaturated alcohols from UV photoelectron spectroscopy

Kowski, Klaus; Lüttke, Wolfgang; Rademacher, Paul

doi:10.1016/s0022-2860(01)00556-7

Cited by 27 publications

(34 citation statements)

References 47 publications

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“…[3,5–7a]) roles in determining molecular conformations, in several chemical and biological processes8 including molecular recognition7b,c and the activity of biomacromolecules,3, 9 and in the stabilization of inclusion complexes 10. OH···π IHBs have significant influence on the preferred orientation of the portion containing a π system, with respect to the rest of the molecule, when the π system can come sufficiently close to a donor OH to interact with it11–15; their strength is ≤5 kcal/mol 16…”

Section: Introductionmentioning

confidence: 98%

Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols

Mammino

Kabanda

2011

Int J of Quantum Chemistry

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Acylphloroglucinols (ACPLs) are polyphenolic compounds derivative from phloroglucinol, characterized by the presence of at least one COR group and exhibiting a variety of biological activities, which makes them interesting for drug development possibilities. This study investigates patterns in the ways in which weaker intramolecular hydrogen bonds contribute to their conformational stabilization, considering the CH···O H‐bonds, present in all ACPLs, and the OH···π H‐bonds, present in ACPLs in which one or more substituents contain a π bond or system sufficiently close to a phenol OH for the H‐bond to be possible. The results in vacuo and in three different solvents (chloroform, acetonitrile, and water) show that, whereas CH···O plays a significant roles in all these media, the role of OH···π decreases with increasing solvent polarity. Calculations in vacuo are performed at various levels to enable performance comparisons; calculations in solution use the polarizable continuum model. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2011

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Section: Introductionmentioning

confidence: 98%

Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols

Mammino

Kabanda

2011

Int J of Quantum Chemistry

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“…As such, it is reasonable to assume that an interaction between the OH group in carbon C 5 and the benzyl group in C 3 may occur. This interaction, reported in the literature as an intramolecular OH· · ·π hydrogen bond, [43] should be much stronger in compound 4 (aromatic ring substituent: benzyl group) than in compound 3 (one double bond substituent: allyl group).…”

Section: Protonated Compounds 3 Andmentioning

confidence: 89%

Furanose C—C‐linked γ‐lactones: a combined ESI FTICR MS and semi‐empirical calculations study

Madeira¹,

Xavier²,

Rauter³

et al. 2010

J. Mass Spectrom.

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Sugars that incorporate the unsaturated carbonyl motif have become important synthetic targets not only as a result of their potential biological properties but also as precursors in the synthesis of many bioactive products. Moreover, little is known about the influence of the γ-lactone moiety in the fragmentation pattern of furanose rings. Therefore, two α,β-unsaturated γ-lactones (butenolides) and two β-hydroxy γ-lactones, C-C linked to a furanose ring were studied using electrospray ionization FTICR mass spectrometry. The behaviour of the protonated and sodiated forms of the compounds under study has been compared considering their structural features. Fragmentation mechanisms were established and ion structures were proposed taking into account the MS(2) and MS(3) experiments, accurate mass measurements and semi-empirical calculations. These inexpensive methods proved to be a valuable resource for proposing protonation sites and for the establishment of fragmentation pathways.

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“…Compounds 1 ± 6 each possess a hydroxymethyl group at C2 and an ethyl (1,2), vinyl (3,4) or ethynyl group (5,6) at C5. The diastereomeric pairs differ only in the configuration of carbon C2 to which the hydroxymethyl group is attached.…”

Section: Photoelectron Spectra and Electronic Structure Of Some Diastmentioning

confidence: 99%

“…Previously, we have found this level of theory to be adequate for investigations of this type, in particular for intramolecular hydrogen bonds. [6,7] The probably even better MP2(FULL)/6-31 G(2df,p) method proved to be too expansive for molecules of this size. The structures of 1 ± 6 are quite similar.…”

Section: Molecular Structuresmentioning

confidence: 99%

Photoelectron Spectra and Electronic Structure of Some Diastereomeric Quinuclidine Derivatives

et al. 2002

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Evidence for intramolecular OH⋯π hydrogen bonding in unsaturated alcohols from UV photoelectron spectroscopy

Cited by 27 publications

References 47 publications

Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols

Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols

Furanose C—C‐linked γ‐lactones: a combined ESI FTICR MS and semi‐empirical calculations study

Photoelectron Spectra and Electronic Structure of Some Diastereomeric Quinuclidine Derivatives

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