Ab initio and molecular mechanics study of 1,2-dimethoxyethane and 12-crown-4

Bultinck, Patrick; Goeminne, A. M.; Vondel, Dirk Van de

doi:10.1016/s0166-1280(98)00512-0

Cited by 21 publications

(55 citation statements)

References 27 publications

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“…DME and 12-crown-4 were studied previously using the same methods as the ones used here. 4 We found that the ethylene bridges exhibit tGt structures in the COCCOC atom sequence, and that DME and 12-crown-4 both exhibit intramolecular C-H‚‚‚O interactions.…”

Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 72%

“…Stochastic searches were applied previously by Hay et al, 10 and by the present authors for different macrocyclic molecules. 4,6 The reason we applied a combination of stochastic and the systematic search is to cover as much as possible of the molecular PES by furnishing the stochastic searches with different starting minimum energy geometries.…”

Section: Methodsmentioning

confidence: 99%

“…In DME we found 1,5 C-H‚‚‚O interactions. 4 Such interactions are absent in DMP. On the other hand, 1,6 C-H‚‚‚O interactions may be present in DMP.…”

Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 99%

“…The conformational preference of the ethylene type bridges in 14-crown-4 (preference for 0+0 type combinations) is in good agreement with findings for 1,2-dimethoxyethane (DME). 4 It should be noted that the cyclic structure naturally prohibits the presence of some geometries for the ethylene and propylene bridges. Concerning the presence of the stabilizing C-H‚‚‚O interactions, we find that NPA charges point to the existence of these stabilizing interactions as we described earlier for DME and 12-crown-4 4 and DMP (see above).…”

Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 99%

“…These properties are certainly of fundamental interest, since they are likely to influence the characteristics of the complexation (e.g., preorganization). They are also interesting by themselves because macrocycles tend to exhibit some striking features influencing the energetic order of different conformations, e.g., 1,5 C-H‚‚‚O interactions 4,5 and intramolecular electrostatic interactions. 6 This work aims at further investigating the properties of macrocyclic crown ethers by conducting conformational searches using molecular mechanics and by performing an ab initio study of the lowest energy minima using polarized basis sets.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Conformational Analysis of 1,3-Dimethoxypropane and 14-Crown-4: Importance of Stabilizing Intramolecular Interactions

2001

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Results of the theoretical conformational analysis of 14-crown-4 are presented. Conformational analysis was performed using molecular mechanics (MM3) and using two conformational search techniques. The lowest energy minima obtained are submitted to HF/6-31G** calculations, and further optimized. Results are discussed with emphasis on the importance of intramolecular interactions, and the energetic order of conformations is explained on the basis of findings for 1,2-dimethoxyethane and 1,3-dimethoxypropane.

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Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 72%

Section: Methodsmentioning

confidence: 99%

“…In DME we found 1,5 C-H‚‚‚O interactions. 4 Such interactions are absent in DMP. On the other hand, 1,6 C-H‚‚‚O interactions may be present in DMP.…”

Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 99%

Section: 3-dimethoxypropane and Intramolecular C-h‚‚‚omentioning

confidence: 99%