Hydrogen/deuterium isotope effects on the 15N NMR chemical shifts and geometries of low-barrier hydrogen bonds in the solid state

Benedict, Hans; Hoelger, Christoph; Aguilar‐Parrilla, Francisco; Fehlhammer, Wolf Peter; Wehlan, Martin; Janoschek, Rudolf; Limbach, Hans−Heinrich

doi:10.1016/0022-2860(95)09143-2

Cited by 39 publications

(49 citation statements)

References 34 publications

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“…Nuclear magnetic resonance of 15 N as well as 'H and C, and also nuclear quadrupole resonance of 2 H and l4 N are very useful for the study of N-H -• -N hydrogen bonding, as pointed out in [2], and a number of experimental and theoretical studies were conducted on the imidazole family and related materials in solution [13,14] and in the solid state [12,[15][16][17][18][19][20][21][22][23][24][25][26][27][28].…”

Section: H Imentioning

confidence: 99%

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

Nakamura

Masui

Ueda

2000

Zeitschrift Für Naturforschung A

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Ab initio Hartree-Fock molecular orbital calculations were applied to the crystalline imidazole and its derivatives in order to examine systematically the effect of possible N-H---N type hydrogen bonding on the nuclear quadrupole interaction parameters in these materials. The nitrogen quadrupole coupling constant (QCC) and the asymmetry parameter (r?) of the electric field gradient (EFG) were found to depend strongly on the size of the molecular clusters, from single molecule, to dimer, trimer and to the infinite molecular chain, i.e., crystalline state, implying that the intermolecular N-H -N hydrogen bond affects significantly the electronic structure of imidazole molecule. A certain correlation between the QCC of l4 N and the N-H bond distance R was also found and interpreted on the basis of the molecular orbital theory. However, we found that the value of the calculated EFG at the hydrogen position of the N-H group, or the corresponding QCC value of 2 H, increases drastically as /C* when R is shorter than about 0.1 nm, due probably to the inapplicability of the Gaussian basis sets to the very short chemical bond as revealed in the actual imidazole derivatives. We suggested that the observed N-H distances in imidazole derivatives should be re-examined.

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Section: H Imentioning

confidence: 99%

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

Nakamura

Masui

Ueda

2000

Zeitschrift Für Naturforschung A

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“…Nuclear magnetic resonance as well as nuclear quadrupole resonance, which probe nuclei such as 1 H, 2 H, 13 C, 14 N, and 15 N in the imidazole molecule, give useful information on the local structure, dynamic properties, and electronic structure for the N-H· · · N type hydrogen bond [2]. A number of experimental and theoretical studies have been conducted on the imidazole family and related materials in solutions [9,10] and in crystals [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

One- and Two-Dimensional 15N Exchange CP/MAS NMR Studies of the Structure and Electronic Properties of the Intermolecular N—H⋯N Hydrogen Bond in Imidazole Crystal

Ueda

Masui

Nakamura

2001

Solid State Nuclear Magnetic Resonance

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“…13 Figure 1 shows the plot of  15 N(D) vs 1 J 15 N, 1 H) obtained for the Schiff bases studied previously in solution. 13 -15 For the pure NH form, 1 J 15 N, 1 H ³ 90 Hz, 13 -16 whereas for the pure OH form, the coupling constant 16,17 In this work, we undertook a study of the deuterium isotope effect  15 N(D) in order to obtain information on the tautomerism in symmetric (1-4) and unsymmetric (5) (Fig. 1) helped us to estimate the position of the proton transfer equilibrium.…”

Section: Discussionmentioning

confidence: 99%

“…To the best of our knowledge, only a few measurements of the deuterium isotope effect in the solid state have been reported. 5,6 The aim of this study was to detect the possible proton transfer equilibrium and interactions between the two hydrogen bonds in the solid state. The importance of studying proton transfer in the solid state is related to possible applications of Schiff bases.…”

Section: Introductionmentioning

confidence: 99%

Deuterium isotope effects on ¹⁵N chemical shifts of double Schiff bases in the solid state and solution

Dziembowska¹,

Ambroziak²,

Rozwadowski³

et al. 2003

Magnetic Reson in Chemistry

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The proton transfer equilibrium in a series of double Schiff base derivatives of trans-1,2-diaminocyclohexane in solution and the solid state was studied by means of 15 N NMR spectroscopy and analysis of the deuterium isotope effect on the chemical shifts 1 15 N(D). The presence of a proton transfer equilibrium in the N-2-hydroxynaphthylidene moieties of the Schiff bases studied in the solid state at room temperature was evidenced. The results confirmed the interrelation of the two hydrogen bonds in double Schiff base derivatives of trans-1,2-diaminocyclohexane.

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Hydrogen/deuterium isotope effects on the 15N NMR chemical shifts and geometries of low-barrier hydrogen bonds in the solid state

Cited by 39 publications

References 34 publications

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

One- and Two-Dimensional 15N Exchange CP/MAS NMR Studies of the Structure and Electronic Properties of the Intermolecular N—H⋯N Hydrogen Bond in Imidazole Crystal

Deuterium isotope effects on ¹⁵N chemical shifts of double Schiff bases in the solid state and solution

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Hydrogen/deuterium isotope effects on the 15N NMR chemical shifts and geometries of low-barrier hydrogen bonds in the solid state

Cited by 39 publications

References 34 publications

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

Effect of Intermolecular Hydrogen Bonding on the Nuclear Quadrupole Interaction in Imidazole and its Derivatives as Studied by ab initio Molecular Orbital Calculations

One- and Two-Dimensional 15N Exchange CP/MAS NMR Studies of the Structure and Electronic Properties of the Intermolecular N—H⋯N Hydrogen Bond in Imidazole Crystal

Deuterium isotope effects on 15N chemical shifts of double Schiff bases in the solid state and solution

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Deuterium isotope effects on ¹⁵N chemical shifts of double Schiff bases in the solid state and solution