Attractive Inter- and Intramolecular N.cntdot..cntdot..cntdot.O Interactions in N,N-Dipicrylamine and Its Ionic Complexes

Woźniak, Krzysztof; He, Heyong; Klinowski, Jacek; Jones, W. Glyn; Grech, E.

doi:10.1021/j100102a049

Cited by 66 publications

(47 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3). The NÁÁÁO interaction angle (O-NÁÁÁO, C-NÁÁÁO) values are in agreement with those previously reported for similar interactions, being close to 90° [15]; however, a very short NÁÁÁO distance of 2.7536(12) Å is observed. Although the sum of the van der Waals radii of oxygen and nitrogen atoms is 3.07 Å [16], the NÁÁÁO interactions are considered to be significantly stabilizing if the distance is less than 3.5 Å [15,17].…”

Section: Crystal Structure Ofsupporting

confidence: 92%

Synthesis and crystal structures of two isomeric nitro-α-resorcylic acids

et al. 2008

View full text Add to dashboard Cite

Nitration of a-resorcylic acid (3,5-dihydroxybenzoic acid) to 3,5-dihydroxy-2-nitrobenzoic acid (1) and 3,5-dihydroxy-4-nitrobenzoic acid (2), their separation, and crystallization is described. Crystal structures of 1, 1 Á 3H 2 O, and 2 were determined by X-ray single-crystal diffraction analysis and compared with DFT-calculated structures. An intramolecular hydrogen bond between the nitro group and o-hydroxyl group(s) occurs in all investigated structures. Intermolecular hydrogen bonds and pÁÁÁp stacking interactions determine the molecular packing. Additionally, NÁÁÁO interactions have a crucial role in arrangement of the molecules in the crystal structures of 1 and 2. DFT calculations in the gas phase and in the solution reveal that minor product 2 is a more stable regioisomer than 1, the major product in the nitration reaction.

show abstract

Section: Crystal Structure Ofsupporting

confidence: 92%

Synthesis and crystal structures of two isomeric nitro-α-resorcylic acids

et al. 2008

View full text Add to dashboard Cite

show abstract

“…In Table III are given the separations of the atoms involved in attractive interactions in dimers I and II, as well as the interaction energies at 0 K and enthalpies at 298 K. Dimer I is the result of four interactions, two O---H and two O---N. The separations in the latter two are within the range for O---N attractive interactions, 2.85 to 3.40 Å, that has been observed in crystallographic studies of nitrosubstituted molecular solids [56]. Dimer II involves just two O---H interactions and is less strongly bound than I.…”

Section: Dimers Of Dimethylnitraminementioning

confidence: 57%

“…Our search for dimethylnitramine dimers accordingly focused upon such configurations. (The existence of O---H-C hydrogen bonding [53 -55] and attractive intermolecular O---N interactions between nitro groups [56] are both well-established. )…”

Section: Molecular Surface Electrostatic Potential Of Dimethylnitraminementioning

confidence: 99%

Density functional study of dimers of dimethylnitramine

Politzer

Concha

Murray

2000

Int. J. Quantum Chem.

View full text Add to dashboard Cite

“…RDX binding is mediated only partially by the electrostatic interactions between this oxygen, carbonyl [71]. In the systems containing the aromatic nitro derivatives the O…O contacts were suggested to be a consequence of the N…O contacts [72]. Comparable orientation of RDX interacting with IRMOF-1(Zn) was suggested in another theoretical study [35] where Zn-O distance is ∼2.0 Å between a Zn atom of connector and O(N-O 2 ) atom of RDX.…”

Section: Intermolecular Interactionsmentioning

confidence: 94%

Molecular simulations of adsorption of RDX and TATP on IRMOF-1(Be)

et al. 2012

View full text Add to dashboard Cite

The influence of different sorption sites of isoreticular metal-organic frameworks (IRMOFs) on interactions with explosive molecules is investigated. Different connector effects are taken into account by choosing IRMOF-1(Be) (IRMOF-1 with Zn replaced by Be), and two high explosive molecules: 1,3,5-trinitro-s-triazine (RDX) and triacetone triperoxide (TATP). The key interaction features (structural, electronic and energetic) of selected contaminants were analyzed by means of density functional calculations. The interaction of RDX and TATP with different IRMOF-1(Be) fragments is studied. The results show that physisorption is favored and occurs due to hydrogen bonding, which involves the C-H groups of both molecules and the carbonyl oxygen atoms of IRMOF-1(Be). Additional stabilization of RDX and TATP arises from weak electrostatic interactions. Interaction with IRMOF-1(Be) fragments leads to polarization of the target molecules. Of the molecular configurations we have studied, the Be-O-C cluster connected with six benzene linkers (1,4-benzenedicarboxylate, BDC), possesses the highest binding energy for the studied explosives (-16.4 kcal mol(-1) for RDX and -12.9 kcal mol(-1) for TATP). The main difference was discovered to be in the preferable adsorption site for adsorbates (RDX above the small and TATP placed above the big cage). Based on these results, IRMOF-1 can be suggested as an effective material for storage and also for separation of similar explosives. Hydration destabilizes most of the studied adsorption systems by 1-3 kcal mol(-1) but it leads to the same trend in the binding strength as found for the non-hydrated complexes.

show abstract

Attractive Inter- and Intramolecular N.cntdot..cntdot..cntdot.O Interactions in N,N-Dipicrylamine and Its Ionic Complexes

Cited by 66 publications

References 10 publications

Synthesis and crystal structures of two isomeric nitro-α-resorcylic acids

Synthesis and crystal structures of two isomeric nitro-α-resorcylic acids

Density functional study of dimers of dimethylnitramine

Molecular simulations of adsorption of RDX and TATP on IRMOF-1(Be)

Contact Info

Product

Resources

About