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

Kyu Sung Jeong; Young Lag Cho

doi:10.1016/S0040-4039(97)00602-3

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

Kyu Sung Jeong, Young Lag Cho

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

39 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 language	English
Pages (from-to)	3279-3282
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(97)00602-3
Publication status	Published - 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

Access to Document

10.1016/S0040-4039(97)00602-3

Cite this

@article{b0964b18cd664dec84f17b545c5d8b22,

title = "Highly strong complexation of carboxylates with 1-alkylpyridinium receptors in polar solvents",

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.",

author = "Jeong, {Kyu Sung} and Cho, {Young Lag}",

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.",

year = "1997",

month = may,

day = "5",

doi = "10.1016/S0040-4039(97)00602-3",

language = "English",

volume = "38",

pages = "3279--3282",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "18",

}

TY - JOUR

T1 - Highly strong complexation of carboxylates with 1-alkylpyridinium receptors in polar solvents

AU - Jeong, Kyu Sung

AU - Cho, Young Lag

N1 - 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.

PY - 1997/5/5

Y1 - 1997/5/5

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0030944454&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030944454&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)00602-3

DO - 10.1016/S0040-4039(97)00602-3

M3 - Article

AN - SCOPUS:0030944454

SN - 0040-4039

VL - 38

SP - 3279

EP - 3282

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this