Macroscopic and microscopic ionization constants of the thiol and amine groups in 1-methyl-4-mercaptopiperidine
The acid dissociation constants of 1-methyl-4-mercaptopiperidine (p K 1 = 9.51, p K 2 = 11.33), the 1,1-dimethyl-4-mercaptopiperidinium ion (p K A = 9.59) and 1-methyl-4-(methylthio)piperidine (p K B = 10.18) have been determined potentiometrically in 3 M sodium perchlorate (10% methanol) medium. Th...
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| Veröffentlicht in: | Talanta (Oxford) 1983-07, Vol.30 (7), p.537-542 |
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| creator | Barrera, H. Bayon, J.C. Gonzalez-Duarte, P. Sola, J. Vives, J. |
| description | The acid dissociation constants of 1-methyl-4-mercaptopiperidine (p
K
1 = 9.51, p
K
2 = 11.33), the 1,1-dimethyl-4-mercaptopiperidinium ion (p
K
A = 9.59) and 1-methyl-4-(methylthio)piperidine (p
K
B = 10.18) have been determined potentiometrically in 3
M sodium perchlorate (10% methanol) medium. The ultraviolet absorption of the mercaptide ion has been used to determine the relative proton affinity of the sulphur and nitrogen functions in 1-methyl-4-mercaptopiperidine under the same conditions, and its four microscopic constants (p
K
a = 9.49, p
K
b = 10.23, p
K
c = 11.34, p
K
d = 10.60) have been calculated; p
K
A has also been determined spectrophotometrically. From the results obtained, it can be concluded that the thiol group is more acidic than the amine group and that the Adams relation,
K
a +
K
b =
K
1, holds very well when it is assumed that the spectrophotometric values for
K
a, and
K
b, can be replaced by
K
A and
K
B respectively. |
| doi_str_mv | 10.1016/0039-9140(83)80127-1 |
| format | Article |
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K
1 = 9.51, p
K
2 = 11.33), the 1,1-dimethyl-4-mercaptopiperidinium ion (p
K
A = 9.59) and 1-methyl-4-(methylthio)piperidine (p
K
B = 10.18) have been determined potentiometrically in 3
M sodium perchlorate (10% methanol) medium. The ultraviolet absorption of the mercaptide ion has been used to determine the relative proton affinity of the sulphur and nitrogen functions in 1-methyl-4-mercaptopiperidine under the same conditions, and its four microscopic constants (p
K
a = 9.49, p
K
b = 10.23, p
K
c = 11.34, p
K
d = 10.60) have been calculated; p
K
A has also been determined spectrophotometrically. From the results obtained, it can be concluded that the thiol group is more acidic than the amine group and that the Adams relation,
K
a +
K
b =
K
1, holds very well when it is assumed that the spectrophotometric values for
K
a, and
K
b, can be replaced by
K
A and
K
B respectively.</description><identifier>ISSN: 0039-9140</identifier><identifier>EISSN: 1873-3573</identifier><identifier>DOI: 10.1016/0039-9140(83)80127-1</identifier><identifier>PMID: 18963415</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><ispartof>Talanta (Oxford), 1983-07, Vol.30 (7), p.537-542</ispartof><rights>1983</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-90b1a62b29682f85bf52759e0c8c58296c9307d5d52db1e363cb5ac7cd472bef3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0039914083801271$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18963415$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Barrera, H.</creatorcontrib><creatorcontrib>Bayon, J.C.</creatorcontrib><creatorcontrib>Gonzalez-Duarte, P.</creatorcontrib><creatorcontrib>Sola, J.</creatorcontrib><creatorcontrib>Vives, J.</creatorcontrib><title>Macroscopic and microscopic ionization constants of the thiol and amine groups in 1-methyl-4-mercaptopiperidine</title><title>Talanta (Oxford)</title><addtitle>Talanta</addtitle><description>The acid dissociation constants of 1-methyl-4-mercaptopiperidine (p
K
1 = 9.51, p
K
2 = 11.33), the 1,1-dimethyl-4-mercaptopiperidinium ion (p
K
A = 9.59) and 1-methyl-4-(methylthio)piperidine (p
K
B = 10.18) have been determined potentiometrically in 3
M sodium perchlorate (10% methanol) medium. The ultraviolet absorption of the mercaptide ion has been used to determine the relative proton affinity of the sulphur and nitrogen functions in 1-methyl-4-mercaptopiperidine under the same conditions, and its four microscopic constants (p
K
a = 9.49, p
K
b = 10.23, p
K
c = 11.34, p
K
d = 10.60) have been calculated; p
K
A has also been determined spectrophotometrically. From the results obtained, it can be concluded that the thiol group is more acidic than the amine group and that the Adams relation,
K
a +
K
b =
K
1, holds very well when it is assumed that the spectrophotometric values for
K
a, and
K
b, can be replaced by
K
A and
K
B respectively.</description><issn>0039-9140</issn><issn>1873-3573</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLxDAUhYMozvj4ByLdqYtqHk2bbgQZfIHiRtchTW410jY1SQX99Wacwdm5uNyb8J1zuQehI4LPCSblBcaszmtS4FPBzgQmtMrJFpoTUbGc8Ypto_kfMkN7IbxjjCnDbBfNiKhLVhA-R-5Rae-CdqPVmRpM1tvN27rBfquYWqbdEKIaYshcm8U3SGVd96tQvR0ge_VuGkNmh4zkPcS3ry4v0uC1GmMyG8Fbk7gDtNOqLsDhuu-jl5vr58Vd_vB0e7-4esg1K0nMa9wQVdKG1qWgreBNy2nFa8BaaC7Sr64Zrgw3nJqGACuZbrjSlTZFRRto2T46WfmO3n1MEKLsbdDQdWoANwVZMSZo8qwTWazI5d3BQytHb3vlvyTBcpm0XMYolzFKweRv0pIk2fF6wdT0YDaidbQJuFwBkM78tOBl0BYGDcZ60FEaZ__f8AN1eo6V</recordid><startdate>198307</startdate><enddate>198307</enddate><creator>Barrera, H.</creator><creator>Bayon, J.C.</creator><creator>Gonzalez-Duarte, P.</creator><creator>Sola, J.</creator><creator>Vives, J.</creator><general>Elsevier B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>198307</creationdate><title>Macroscopic and microscopic ionization constants of the thiol and amine groups in 1-methyl-4-mercaptopiperidine</title><author>Barrera, H. ; Bayon, J.C. ; Gonzalez-Duarte, P. ; Sola, J. ; Vives, J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-90b1a62b29682f85bf52759e0c8c58296c9307d5d52db1e363cb5ac7cd472bef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barrera, H.</creatorcontrib><creatorcontrib>Bayon, J.C.</creatorcontrib><creatorcontrib>Gonzalez-Duarte, P.</creatorcontrib><creatorcontrib>Sola, J.</creatorcontrib><creatorcontrib>Vives, J.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Talanta (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barrera, H.</au><au>Bayon, J.C.</au><au>Gonzalez-Duarte, P.</au><au>Sola, J.</au><au>Vives, J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Macroscopic and microscopic ionization constants of the thiol and amine groups in 1-methyl-4-mercaptopiperidine</atitle><jtitle>Talanta (Oxford)</jtitle><addtitle>Talanta</addtitle><date>1983-07</date><risdate>1983</risdate><volume>30</volume><issue>7</issue><spage>537</spage><epage>542</epage><pages>537-542</pages><issn>0039-9140</issn><eissn>1873-3573</eissn><abstract>The acid dissociation constants of 1-methyl-4-mercaptopiperidine (p
K
1 = 9.51, p
K
2 = 11.33), the 1,1-dimethyl-4-mercaptopiperidinium ion (p
K
A = 9.59) and 1-methyl-4-(methylthio)piperidine (p
K
B = 10.18) have been determined potentiometrically in 3
M sodium perchlorate (10% methanol) medium. The ultraviolet absorption of the mercaptide ion has been used to determine the relative proton affinity of the sulphur and nitrogen functions in 1-methyl-4-mercaptopiperidine under the same conditions, and its four microscopic constants (p
K
a = 9.49, p
K
b = 10.23, p
K
c = 11.34, p
K
d = 10.60) have been calculated; p
K
A has also been determined spectrophotometrically. From the results obtained, it can be concluded that the thiol group is more acidic than the amine group and that the Adams relation,
K
a +
K
b =
K
1, holds very well when it is assumed that the spectrophotometric values for
K
a, and
K
b, can be replaced by
K
A and
K
B respectively.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>18963415</pmid><doi>10.1016/0039-9140(83)80127-1</doi><tpages>6</tpages></addata></record> |
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| ispartof | Talanta (Oxford), 1983-07, Vol.30 (7), p.537-542 |
| issn | 0039-9140 1873-3573 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733825279 |
| source | Elsevier ScienceDirect Journals Complete |
| title | Macroscopic and microscopic ionization constants of the thiol and amine groups in 1-methyl-4-mercaptopiperidine |
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