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Investigation of molecular interactions in the complex formation of tartaric acid derivatives with di(2-ethylhexyl) phosphoric acid

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Abstract

The molecular interactions in the complex formation of two tartaric acid derivatives with di(2-ethylhexyl) phosphoric acid are investigated. The complex formation with a 1:1 stoichiometry between tartaric acid derivatives and D2EHPA can be obtained through UV-Vis titration, NMR chemical shifts and molecular dynamic simulations. Furthermore, the differences of the two complexes on the binding constants and strength of hydrogen bonds can also be determined. Such research will ideally provide insight into ways of regulating the complex forming properties of tartaric acid derivatives for composing or synthesizing new chiral resolving agents.

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References

  1. Jacques J, Collet A, Wilen S H. Enantiomers, Racemates and Resolutions. New York: Wiley and Sons, 1981

    Google Scholar 

  2. Nemák K, Ács M, Jászay Z, Kozma D, Fogassy E. Study of the diastereoisomers formed between (N-alkyl)-pipecolic acid-anilides and 2R,3R-tartaric acid or O,O-dibenzoyl-(2R,3R)-tartaric acid. Do the tartaricacids form molecular-complexes, instead of salts during optical resolutions? Tetrahedron, 1996, 52: 1637–1642

    Article  Google Scholar 

  3. Csaba K, Zoltán J, József B, Elemér F and Dávid K. Optical resolution of racemic alcohols via diastereoisomeric supramolecular compound formation with O,O′-Dibenzoyl-(2R,3R)-tartaric acid. Tetrahedron, 2000, 56: 8355–8359

    Article  Google Scholar 

  4. Tan B, Luo G S, Qi X, Wang J D. Enantioselective extraction of d,l-tryptophan by a new chiral selector: complex formation with di(2-ethylhexyl)phosphoric acid and O,O′-dibenzoyl-(2R,3R)-tartaric acid. Sep Puri T, 2006, 49: 186–191

    Article  CAS  Google Scholar 

  5. Tan B, Luo G S, Wang J D. Enantioseparation of amino acids by co-extractants with di(2-ethylhexyl)phosphoric acid and tartaric acid derivatives. Tetrahedron: Asymmetry, 2006, 17: 883–891

    Article  CAS  Google Scholar 

  6. Tan B, Luo G S, Wang J D. Extractive separation of amino acid enantiomers with co-extractants of tartaric acid derivative and Aliquat-336. Sep Puri T, 2007, 53: 330–336

    Article  CAS  Google Scholar 

  7. Andrá M, Zsolt B, Zoltán K, Imre M, Elemér F. Coordination-mediated optical resolution of carboxylic acids with O,O′-dibenzoyltartaric acid. Angew Chem Int Ed, 1997, 36: 1534–1536

    Article  Google Scholar 

  8. Benesi H A, Hildebrand J H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc, 1949, 71: 2703–2707

    Article  CAS  Google Scholar 

  9. Vaton -C L, Oulyadi H, Combret Y, Coquerel G, Combret J C. Chiral recognition of binaphthyl derivatives: A chiral recognition model on the basis of chromatography, spectroscopy, and molecular mechanistic calculations for the enantioseparation of 1,1′-binaphthyl derivatives on cholic acid-bonded stationary phases. Chirality, 2001, 13: 668–674

    Article  Google Scholar 

  10. Du J T, Li Y M, Wei W, Wu G S, Zhao Y F, Kanazawa K, Nemoto T, Nakanishi H. Low-barrier hydrogen bond between phosphate and the amide group in phosphopeptide. J Am Chem Soc, 2005, 127: 16350–16351

    Article  CAS  Google Scholar 

  11. Sun H. Compass: an ab initio force-field optimized for condensed phase applications-overview with details on alkane and benzene compounds. J Phys Chem B, 1998, 102: 7338–7364

    Article  CAS  Google Scholar 

  12. Rigby D, Sun H, Eichinger B E. Computer simulations of poly(ethylene oxide): force field, pvt diagram and cyclization behaviour. Polym Int, 1997, 44(3): 311–330

    Article  CAS  Google Scholar 

  13. Sumie Y, Yukio A, Shigeo K. Prediction of glass transition temperature of freeze-dried formulations by molecular dynamics simulation. Pharm Res, 2003, 20: 873–878

    Article  Google Scholar 

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Correspondence to GuangSheng Luo.

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Supported by the National Basic Research Program of China (Grant No. 2007CB714302) and the National Natural Science Foundation of China (Grant Nos. 20676066 & 20525622)

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Tan, B., Zhai, Z., Luo, G. et al. Investigation of molecular interactions in the complex formation of tartaric acid derivatives with di(2-ethylhexyl) phosphoric acid. Sci. China Ser. B-Chem. 51, 887–892 (2008). https://doi.org/10.1007/s11426-008-0066-8

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  • DOI: https://doi.org/10.1007/s11426-008-0066-8

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