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

被引：13

作者：

Jozwiak, Kinga ^{[1
]}

Jezierska, Aneta ^{[1
]}

Panek, Jaroslaw J. ^{[1
]}

Goremychkin, Eugene A. ^{[2
]}

Tolstoy, Peter M. ^{[3
]}

Shenderovich, Ilya G. ^{[4
]}

Filarowski, Aleksander ^{[1
]}

机构：

[1] Univ Wroclaw, Fac Chem, 14 F Joliot Curie Str, PL-50383 Wroclaw, Poland

[2] Joint Inst Nucl Res, Frank Lab Neutron Phys, 6 F Joliot Curie Str, Dubna 141980, Russia

[3] St Petersburg State Univ, Inst Chem, Univ Skij Pr 26, St Petersburg 198504, Russia

[4] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany

来源：

MOLECULES | 2020年 / 25卷 / 20期

基金：

俄罗斯科学基金会; 俄罗斯基础研究基金会;

关键词：

proton dynamics; carboxyl group; CPMD; DFT; IINS; IR; Raman; NMR; INELASTIC NEUTRON-SCATTERING; MOLECULAR-ORBITAL METHODS; POLARIZED IR-SPECTRA; NMR CHEMICAL-SHIFTS; X-RAY-DIFFRACTION; INFRARED-SPECTRA; VIBRATIONAL-SPECTRA; CRYSTAL-STRUCTURES; SALICYLIC-ACID; ACETIC-ACID;

D O I：

10.3390/molecules25204720

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：22

共 30 条

[21] Recurrent Supramolecular Motifs in a Series of Acid Base Adducts Based on Pyridine-2,5-Dicarboxylic Acid N-Oxide and Organic Bases: Inter- and Intramolecular Hydrogen Bonding
Mirzaei, Masoud
Sadeghi, Fereshteh
Molcanov, Kresimir
Zareba, Jan K.
Gomila, Rosa M.
Frontera, Antonio
CRYSTAL GROWTH & DESIGN, 2020, 20 (03) : 1738 - 1751
[22] The Role of Intramolecular Hydrogen Bonds vs. Other Weak Interactions on the Conformation of Hyponitrous Acid and Its Mono- and Dithio-Derivatives
Jenny Zevallos
Alejandro Toro-Labbé
Otilia Mó
Manuel Yáñez
Structural Chemistry, 2005, 16 : 295 - 303
[23] The role of intramolecular hydrogen bonds vs. other weak interactions on the conformation of hyponitrous acid and its mono- and dithio-derivatives
Zevallos, J
Toro-Labbé, A
Mó, O
Yáñez, M
STRUCTURAL CHEMISTRY, 2005, 16 (03) : 295 - 303
[24] Comparison of interaction patterns of a triblock copolymer micelle with zwitterionic vs. cationic surfactant: An excited-state proton transfer dynamics investigation
Pal, Tapas
Sahu, Kalyanasis
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2022, 640
[25] Two Modifications of Nitrilotris(methylenephenylphosphinic) Acid: A Polymeric Network with Intermolecular (O=P-O-H)3 vs. Monomeric Molecules with Intramolecular (O=P-O-H)3 Hydrogen Bond Cyclotrimers
Knerr, Steven
Brendler, Erica
Gericke, Robert
Kroke, Edwin
Wagler, Joerg
CRYSTALS, 2024, 14 (07)
[26] Proton dynamics in the strong chelate hydrogen bond of crystalline picolinic acid N-oxide.: A new computational approach and infrared, Raman and INS study
Stare, Jernej
Panek, Jaroslaw
Eckert, Juergen
Grdadolnik, Joze
Mavri, Janez
Hadzi, Dusan
JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (07): : 1576 - 1586
[27] Application of schrodinger equation to study the tunnelling dynamics of proton transfer in the hydrogen bond of 2,5-dinitrobenzoic acid:: Proton T1, T1ρ, and deuteron T1 relaxation methods
Latanowicz, L.
Medycki, W.
JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (07): : 1351 - 1357
[28] From the isolated molecule to oligomers and the crystal:: A static density functional theory and Car-Parrinello molecular dynamics study of geometry and potential function modifications of the short intramolecular hydrogen bond in picolinic acid N-oxide
Panek, J
Stare, J
Hadzi, D
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (36): : 7417 - 7423
[29] Ab initio and MS/MS studies on protonated peptides containing basic and acidic amino acid residues I.: Solvated proton vs. salt-bridged structures and the cleavage of the terminal amide bond of protonated RD-NH2
Paizs, B
Suhai, S
Hargittai, B
Hruby, V
Somogyi, A
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2002, 219 (01) : 203 - 232
[30] THE COMPARATIVE ROLES OF THE PROTON-ACCEPTOR PROPERTIES OF AMIDE AND CARBOXYL GROUPS IN INFLUENCING CRYSTAL PACKING PATTERNS - DOUBLY VS SINGLY HYDROGEN-BONDED SYSTEMS IN N-ACYL AMINO-ACIDS AND IN OTHER AMIDE-ACID CRYSTALS
BERKOVITCHYELLIN, Z
ARIEL, S
LEISEROWITZ, L
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (04) : 765 - 767

← 1 2 3 →