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Walczak D, Nowacki A. DFT studies of conversion of methyl chloride and three substituted chloromethyl tetrahydrofuran derivatives during reaction with trimethylamine. J Mol Model. 2013;19(10):4403-17doi: 10.1007/s00894-013-1940-7.
Walczak, D., & Nowacki, A. (2013). DFT studies of conversion of methyl chloride and three substituted chloromethyl tetrahydrofuran derivatives during reaction with trimethylamine. Journal of molecular modeling, 19(10), 4403-17. https://doi.org/10.1007/s00894-013-1940-7
Walczak, Dominik, and Nowacki, Andrzej. "DFT studies of conversion of methyl chloride and three substituted chloromethyl tetrahydrofuran derivatives during reaction with trimethylamine." Journal of molecular modeling vol. 19,10 (2013): 4403-17. doi: https://doi.org/10.1007/s00894-013-1940-7
Walczak D, Nowacki A. DFT studies of conversion of methyl chloride and three substituted chloromethyl tetrahydrofuran derivatives during reaction with trimethylamine. J Mol Model. 2013 Oct;19(10):4403-17. doi: 10.1007/s00894-013-1940-7. Epub 2013 Aug 06. PMID: 23918221; PMCID: PMC3778228.
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J Mol Model. 2013 Oct;19(10):4403-17. doi: 10.1007/s00894-013-1940-7. Epub 2013 Aug 06.

DFT studies of conversion of methyl chloride and three substituted chloromethyl tetrahydrofuran derivatives during reaction with trimethylamine.

Journal of molecular modeling

Dominik Walczak, Andrzej Nowacki

Affiliations

  1. Faculty of Chemistry, University of Gda?sk, Wita Stwosza 63, 80-952, Gda?sk, Poland.

PMID: 23918221 PMCID: PMC3778228 DOI: 10.1007/s00894-013-1940-7

Abstract

B3LYP/6-31+G level computations were performed for the formation of four trimethylammonium salts in the reaction of methyl chloride (1a), (S)-1,4-andydro-5-chloro-2,3,5-trideoxypentitol (2a), (2S,5S)-2,5-andydro-6-chloro-1,3,4,6-tetradeoxyhexitol (3a) and methyl 5-chloro-2,3,5-trideoxy-β-D-pentofuranoside (4a) with trimethylamine. All the structures were fully optimized in the gas phase, in chloroform and water. In addition, B3LYP/6-311++G and MPW1K/6-31+G level calculations were carried out to estimate activation barrier heights in the gas phase. A detailed description of all stationary points is presented, and the conformational behavior of the THF ring is discussed. B3LYP and MPW1K activation barriers indicate the reaction between methyl chloride and trimethylamine to be the fastest, whereas reaction 4 is the slowest one, both in the gas phase and in solvents. THF ring conformation changes were observed for reactions 2 and 3 along the reaction pathway, whereas it was almost unchanged for reaction 4, in the gas phase. In the case of reactions 2 and 3, different shapes of the THF ring were found for the transition state geometry in the gas phase and in water. The (5) E→E 4 and (3) E→E 5 conformational changes were observed for reactions 2 and 3, respectively.

References

  1. J Phys Chem B. 2010 Jul 1;114(25):8425-30 - PubMed
  2. J Org Chem. 2002 Jul 12;67(14):4647-51 - PubMed
  3. Carbohydr Res. 2006 Aug 14;341(11):1916-21 - PubMed
  4. J Comput Aided Mol Des. 2000 Feb;14(2):123-34 - PubMed
  5. Carbohydr Res. 2004 Jun 1;339(8):1537-44 - PubMed
  6. Acc Chem Res. 2010 Jan 19;43(1):142-51 - PubMed
  7. J Am Chem Soc. 1972 Nov 15;94(23):8205-12 - PubMed
  8. J Phys Chem B. 2006 Feb 2;110(4):1877-88 - PubMed
  9. J Org Chem. 2009 Nov 20;74(22):8522-30 - PubMed
  10. J Mol Model. 2013 Aug;19(8):3015-26 - PubMed
  11. Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789 - PubMed
  12. J Phys Chem A. 2005 Mar 31;109(12):2937-41 - PubMed
  13. J Am Chem Soc. 2010 Aug 18;132(32):11071-82 - PubMed
  14. Carbohydr Res. 2004 Oct 4;339(14):2355-62 - PubMed
  15. J Org Chem. 2005 Dec 9;70(25):10238-46 - PubMed

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