Long-distance inter-hydrogen bond coupling effects in the polarized IR spectra of succinic acid crystals

Flakus, Henryk T.; Hachuła, Barbara; Hołaj-Krzak, Jakub T.

doi:10.1016/j.saa.2015.01.074

Cited by 10 publications

(33 citation statements)

References 19 publications

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“…Stretching vibrations of H-bonds have a high diagnostic value for determination of the nature and strength of these bonds [ 97 , 98 ]. Previously, the spectral manifestations of dimerization and isotopic effects on spectroscopic observables were studied for different molecular systems [ 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 ] including carboxylic acid dimers [ 109 , 110 ]. Upon carboxylic acid dimerization, the structure of the OH stretching band in IR spectra changes most prominently: The narrow band of monomers changes to a broad, intensive, and complex substructured band of dimers shifted to lower wavenumbers.…”

Section: Resultsmentioning

confidence: 99%

Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

et al. 2020

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Noncovalent interactions are among the main tools of molecular engineering. Rational molecular design requires knowledge about a result of interplay between given structural moieties within a given phase state. We herein report a study of intra- and intermolecular interactions of 3-nitrophthalic and 4-nitrophthalic acids in the gas, liquid, and solid phases. A combination of the Infrared, Raman, Nuclear Magnetic Resonance, and Incoherent Inelastic Neutron Scattering spectroscopies and the Car–Parrinello Molecular Dynamics and Density Functional Theory calculations was used. This integrated approach made it possible to assess the balance of repulsive and attractive intramolecular interactions between adjacent carboxyl groups as well as to study the dependence of this balance on steric confinement and the effect of this balance on intermolecular interactions of the carboxyl groups.

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Section: Resultsmentioning

confidence: 99%

Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

et al. 2020

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“…The stability issue of the 4-carbon linker may be derived from the unique planar structure (with a partially non-saturated C–C bonds, involving sp2 hybridized carbon and nitrogen/planar amide bond) of its molecular skeletons, leading to lower reactivity. 27 In this work, we have directly compared THP-derivatives with 5- and 6-carbon linkers. We started with the synthesis of the hexadentate tris (3,4-hydroxypyridinone) ( 2 ) (Fig.…”

Section: Resultsmentioning

confidence: 99%

Targeting integrin αvβ6 with gallium-68 tris (hydroxypyridinone) based PET probes

et al. 2022

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“…This hyperconjugation effect is mainly due to the coplanar structure of succinic acid associations as well as to the characteristics of the C−C bonds, which favor the realization of vibrational couplings within single chains throughout the (COOH) 2 dimers. 25,31 Research on isomeric benzenedicarboxylic acids provided additional confirmation of the accepted argument for the influence of the electronic factor on the mechanism of generating infrared spectra. The infrared spectra obtained for selectively substituting with deuterons of terephthalic acid isotopic varieties confirmed that replacing the para-phenylene ring, occupying the quasi-unsaturated center, effectively governs the H/D isotopic arrangements within the hydrogen bond cycles.…”

Section: Introductionmentioning

confidence: 83%

Elucidating the Infrared Spectral Properties of Succinic Molecular Acid Crystals: Illustration of the Structure and the Hydrogen Bond Energies of the Crystal and Its Deuterated Analogs

et al. 2022

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Herein, the infrared spectroscopic properties of molecular succinic acid crystals (SA) and their four isotopic analogs [C 2 H 4 (COOH) 2 , h 6 -SA; C 2 H 4 (COOD) 2 , d 2 -SA; C 2 D 4 (COOH) 2 , d 4 -SA; C 2 D 4 (COOD) 2 , d 6 -SA] are reported. The correlation between the structure of succinic acid molecules and their corresponding hydrogen bond energies is elucidated. The effects related to the isotopic dilution as well as the changes in the spectrum recording temperature on the fine structures of the v O−H and v O−D bands are interpreted. The infrared spectral anomalies detected in the spectra of isotopically neat succinic nanocrystal acids are confirmed by theoretical calculations using density functional theory (DFT). According to previous spectroscopic studies of succinic acid and those carried out for α,ω-dicarboxylic acids, a decent agreement between the experimental results and the theoretical DFT simulations is obtained. Moreover, the spectra of single crystals of the h 6 and d 4 succinic acid variants prove that the vibrational coupling mechanism between the (COOH) 2 cycles is rigorously convergent to that detected in the spectra of aromatic carboxylic acids, suggesting thereby that the promotion of symmetryforbidden high stretching IR transitions plays a crucial role. Furthermore, the obtained experimental results reveal that the succinic acid shows a spectral behavior significantly different from that characteristic of hydrogen associations of other acids of homologous series, such as the glutaric, adipic, malonic, and pimelic acid crystals. The results obtained herein shed light on the way to explore the revealed structure of isotopic derivatives of succinic acid crystals and may prove to be useful results for understanding the nature of unconventional interactions as well as the macroscopic energy effects directing the development of hydrogen associations.

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Long-distance inter-hydrogen bond coupling effects in the polarized IR spectra of succinic acid crystals

Cited by 10 publications

References 19 publications

Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

Targeting integrin αvβ6 with gallium-68 tris (hydroxypyridinone) based PET probes

Elucidating the Infrared Spectral Properties of Succinic Molecular Acid Crystals: Illustration of the Structure and the Hydrogen Bond Energies of the Crystal and Its Deuterated Analogs

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