Highly strong complexation of carboxylates with 1-alkylpyridinium receptors in polar solvents

Kyu Sung Jeong, Young Lag Cho

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

Mono- and bispyridinium salts are shown to bind strongly with carboxylates in polar media through multiple hydrogen bonds and additional electrostatic interactions. The association constants of monopyridinium salt with various benzoates are in the range of 110-430 M-1 in DMSO-d6, depending on substituents, while those between bispyridinium salts and adipate are >103 M-1 in 10% D2O/DMSO-d6.

Original languageEnglish
Pages (from-to)3279-3282
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number18
DOIs
Publication statusPublished - 1997 May 5

Bibliographical note

Funding Information:
AcknowledgmentT his work was financiallys upportedin part by the Korea Sciencea nd Engineering Foundation(P rojectN o, 96-0501-04-01-0a3n) dthe Basic ScienceR esearchIn stituteP rogram,M inistryof Education(P rojectN o, BSRI-96-3422). Referenceasn d Notes 1. Forreviewsseea): Seel,C .;Gal~tnA, .;deMendozaJ. ,T op.C urr.C hem1. 995,175,101-13b2). (b)Comprehensive SupramoleculCahr emistryA;t woodJ,. L.; DaviesJ,. E. D.; MacNicolD, . D.; V0gdeF, ., Eds.;E lsevieSr cienceLt d.: Oxford,1 996V; ol. 2. For self-assemblisnygn thetrice ceptobrsy multipleh ydrogebno ndss, ee:M eissnerR, .; GarciasX, .; MecozziS. .; RebekJ,. , Jr. J. Am.C hemS. oc.1 997,1197,7 -85a ndr eferencethse rein. 2. For a reviews ee:K irby,A . J. AngewC. hemI.n t.Ed. Engl. 19963, 5,7 07-724. 3. For reviewss ee:a ) MacDonaldJ., C.; WhitesideGs,. M. ChemR. ev.1 9949, 4,2 383-2420b.) FredericksJ., R.; HamiltonA, . D. In ComprehensiSvuep ramoleculCahr emistryA;t woodJ,. L.; DaviesJ,. E. D.; MacNicolD, . D.; V0gtle, F., Eds.;E lsevierS cienceLt d.:O xford,1 996V; ol. 9, pp5 65-621. 4. MetzgerS, .; LippertB, . J. Am.C hemS. oc.1 9961, 18,1 2467-12468. 5. AuffingerP, .; Louise-MayS, . WesthofE, . J. Am.C hemS. oc.1 9961, 18,1 181-1189. 6. a) DesirajuG, . R. Acc. ChemR. es.1 9912, 4,290-296b. ) SteinerT,. ; SaengeWr, .J. Am.C hemS. oc.1 992,1141, 0146-10154c. ) SharmaC, . V. K.; DesirajuG, . R. J. ChemS. oc.,P erkinT rans2. 19942, 345-2352d.) SteinerT, . J. ChemS. oc., PerkinT rans.2 19951, 315-131e9). C haneyJ., D.; Goss,C . R.; FoltingK, .; SantarsierBo., D.; HollingworthM, . D. J. Am. ChemS. oc.1 996,1189,4 32-9433. 7. a) Tayor,R .; KennardO, . J. Am.C hemS. oc.1 9821, 04,5 063-5070b.) PedireddVi,. R.; Jones,W .; ChorltonA, . P.; DochertyR,. J. ChemS. oc.,C hemC. ommun1.9 969, 97-998c. ) SharmaC,. V. K.; ZaworotkoM, . J. J. ChemS. oc., ChemC. ommun1.9 962, 655-2656. 8. Tom~sS,. ; ProhensR, .; Vega,M .; RotgerM, . C.; Dey~P, . M.; BallestePr,. ; CostaA, . J. Org. Chem1. 9966, 1,9 394-9401. 9. Otherb indingm odess ucha sb ifurcatehdy drogebno ndsb etweetnw oo xygena tomos f carboxylaaten dN H mayb ep ossiblaes a refereseu ggested. 10. All compoundwse rer ecrystaUiziend a ppropriasteo lvent(sh exanes/acetoDnMeF, ) beforeti trationsI.n itialc oncentratioonfs hosta ndg ueswt ere5 .0a nd2 5m M in DMSO-d6r, espectively. 11. Kelly,T . R.; Kim, M. H. J. J. Am.C hemS. oc.1 9941, 16.7072-708F2o. r othecr arboxylarteec eptorsse e:a ) Fan.E .; Van armanS, . A.; Kincaid,S .; HamiltonA, . D. J. Am.C hemS. oc.1 9931, 15,369-370b.) J eong,K .-S.;P ark,J . W.; Cbo,Y . L.; TetrahedroLne tt,1 9963, 7.2 795-2798c.) HughesM, . P.; ShangM, .; SmithB, . D. J. Org.C hem1. 9966, 1,4 510-4511. 12. BordwellF, . G. Acc. ChemR. es.1 9882, 1,456-463. 13 Con'orsK, . A. BindingC onstantJso:h nW iley& SonsN: ewY ork, 1984p; 24.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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