Solid state hydrogen bonding in imidazole derivatives: a persistent tape motifElectronic supplementary information (ESI) available: A list of all Cambridge Structural Database codes used in this survey. See http://www.rsc.org/suppdata/ce/b4/b405096g/

Cammers, Arthur; Parkin, Sean

doi:10.1039/b405096g

Cited by 23 publications

(14 citation statements)

References 39 publications

(39 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The calculated hydrogen bond lengths, N 3 ‐H 1 ′‐N 1 ′ angles and C 2 ‐N 3 ‐N 1 ′‐C 2 ′ dihedral angles between the two planes of Im rings, of the most stable dimer Im‐X structures, from up to down gas and acetonitrile phases, are given in Table 1. Hydrogen bond lengths are ∼ 2.0 Å, in agreement with experimental and theoretical results 6–10, 23–25. Short hydrogen bonds tend to have wide Im‐H‐Im bond angles (ca.…”

Section: Resultssupporting

confidence: 88%

See 1 more Smart Citation

Transport properties of trogamid: Comparison of different experimental techniques*

Etxeberria

Garcı́a

Iriarte

et al. 2006

J of Applied Polymer Sci

View full text Add to dashboard Cite

The transport properties of an amorphous polyamide, poly(trymethylhexamethylene terephtalamide) or Trogamid-T, were determined by different experimental methods. Sorption methods included two electrobalances, one for subatmospheric pressures and the other one up to 20 bar, and a pressure decay cell. Also, a permeability cell was used to measure permeability coefficients for pure gases and a gas mixture. The solubility, diffusion, and permeability coefficients calculated by different methods were in good agreement. With regard to permeability, measurements showed the difference between ideal and real permselectivity. Moreover, the results confirmed the good barrier properties of Trogamid-T.

show abstract

Section: Resultssupporting

confidence: 88%

“…Short hydrogen bonds tend to have wide Im‐H‐Im bond angles (ca. 180 ° ) 23. The planes of imidazole rings are almost orthogonal (∼ 90 ° ) for structures in both gas and acetonitrile phases.…”

Section: Resultsmentioning

confidence: 93%

Transport properties of trogamid: Comparison of different experimental techniques*

Etxeberria

Garcı́a

Iriarte

et al. 2006

J of Applied Polymer Sci

View full text Add to dashboard Cite

show abstract

“…The tape motif is a favored solid-state arrangement of hydrogen bonds in molecules possessing the imidazole moiety. [30] This motif connects atoms N1 and N3 by intermolecular hydrogen bonds in a structurally diverse set of imidazole derivatives. [30] However, in the derivatives of 1 studied in this work, some of the N1/N3 intermolecular hydrogen bonds were sacrificed in the solid states to allow for the N1/N12 S (6).…”

Section: Solid-state Studiesmentioning

confidence: 99%

“…[30] This motif connects atoms N1 and N3 by intermolecular hydrogen bonds in a structurally diverse set of imidazole derivatives. [30] However, in the derivatives of 1 studied in this work, some of the N1/N3 intermolecular hydrogen bonds were sacrificed in the solid states to allow for the N1/N12 S (6). In the solid state, derivatives 3 sacrificed the intermolecular hydrogen bond to preferentially establish S(6); derivatives 2 bifurcated the S(6) with the imidazole intermolecular hydrogen bond.…”

Section: Solid-state Studiesmentioning

confidence: 99%

In Search of the Weak, Six‐Membered Intramolecular Hydrogen Bond in the Solution and Solid States of Guanidinobenzimidazole

et al. 2004

Self Cite

View full text Add to dashboard Cite

The chemical literature presents evidence for the nonexistence of the intramolecular hydrogen bond in neutral 2‐guanidinobenzimidazole, a result that defies chemical intuition. In the current study, analyses of substituted 2‐guanidinobenzimidazoles by dynamic 1H NMR, IR, and X‐ray diffraction unveiled the contribution of the intramolecular hydrogen bond to the overall structure and conformational equilibria. The presence of the intramolecular hydrogen bond in this work and its absence in previous studies of the unsubstituted parent compound is reconciled by the fact that intramolecular hydrogen bonds between the imidazole moieties and guanidino NH2 protons were weak. The intramolecular hydrogen bonds were more apparent in derivatives with guanidino NHR. The behavior of the latter indicated competition between and coexistence of inter‐ and intramolecular hydrogen bonding. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

show abstract

“…The 1,3-disposition of the nitrogen atoms in imidazoles leads exclusively to the formation of chains, called catemers [1], while the 1,2-disposition in pyrazoles leads to at least five motives, called cyclamers [2] (Fig. 1, the Etter/Bernstein graph set descriptors are given for each motif) [3,4].…”

Section: Introductionmentioning

confidence: 99%

Proton transfer in C-halogen pyrazole cyclamers. A theoretical study

2007

View full text Add to dashboard Cite

Four monomers and twelve pyrazole cyclamers unsubstituted or bearing fluoro, chloro, or bromo substituents at positions 3 and 5 have been studied at the B3LYP/ 6-31+G** theoretical level. Two mechanisms of proton transfer, stepwise and synchronous, have been studied for dimers, trimers, and tetramers. Even though some values of the barriers have not been determined, the set of values of energies and geometries provide useful insights about the dynamics of NH-pyrazoles in the solid state.

show abstract

Solid state hydrogen bonding in imidazole derivatives: a persistent tape motifElectronic supplementary information (ESI) available: A list of all Cambridge Structural Database codes used in this survey. See http://www.rsc.org/suppdata/ce/b4/b405096g/

Cited by 23 publications

References 39 publications

Transport properties of trogamid: Comparison of different experimental techniques*

Transport properties of trogamid: Comparison of different experimental techniques*

In Search of the Weak, Six‐Membered Intramolecular Hydrogen Bond in the Solution and Solid States of Guanidinobenzimidazole

Proton transfer in C-halogen pyrazole cyclamers. A theoretical study

Contact Info

Product

Resources

About