{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,9,20]],"date-time":"2025-09-20T20:54:34Z","timestamp":1758401674835},"reference-count":31,"publisher":"Elsevier BV","issue":"11","license":[{"start":{"date-parts":[[1988,11,1]],"date-time":"1988-11-01T00:00:00Z","timestamp":594345600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Pharmaceutical Sciences"],"published-print":{"date-parts":[[1988,11]]},"DOI":"10.1002\/jps.2600771105","type":"journal-article","created":{"date-parts":[[2006,10,14]],"date-time":"2006-10-14T18:57:27Z","timestamp":1160852247000},"page":"926-932","source":"Crossref","is-referenced-by-count":10,"title":["Substituent effects on partition coefficients of barbituric acids"],"prefix":"10.1016","volume":"77","author":[{"given":"Ooi","family":"Wong","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert Henry","family":"McKeown","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1002\/jps.2600771105_bb1","series-title":"Advances in Linear Free Energy Relationships","author":"Chapman","year":"1972"},{"key":"10.1002\/jps.2600771105_bb2","doi-asserted-by":"crossref","first-page":"5175","DOI":"10.1021\/ja01077a028","volume":"86","author":"Fujita","year":"1964","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/jps.2600771105_bb3","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1021\/cr60274a001","volume":"71","author":"Leo","year":"1971","journal-title":"Chem. Rev."},{"key":"10.1002\/jps.2600771105_bb4","series-title":"Thesis","author":"Wong","year":"1979"},{"key":"10.1002\/jps.2600771105_bb5","series-title":"M. Pharm.","author":"Prankerd","year":"1976"},{"key":"10.1002\/jps.2600771105_bb6","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.1039\/C39840001440","author":"Buckingham","year":"1984","journal-title":"J. Chem. Soc., Chem. Comm."},{"key":"10.1002\/jps.2600771105_bb7","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1021\/ja00236a027","volume":"109","author":"Buckingham","year":"1987","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/jps.2600771105_bb8","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1039\/P29800000504","author":"McKeown","year":"1980","journal-title":"J. Chem. Soc., Perk. Trans. II"},{"key":"10.1002\/jps.2600771105_bb9","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1021\/jm00317a001","volume":"10","author":"Hansch","year":"1967","journal-title":"J. Med. Chem."},{"key":"10.1002\/jps.2600771105_bb10","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1002\/jps.2600750703","volume":"75","author":"Kim","year":"1986","journal-title":"J. Pharm. Sci."},{"key":"10.1002\/jps.2600771105_bb11","series-title":"Chem. Software Manual","author":"CLOGP program, Med","year":"1985"},{"key":"10.1002\/jps.2600771105_bb12","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1002\/jps.3030490906","volume":"49","author":"Lamb","year":"1960","journal-title":"J. Am. Pharm. Assoc."},{"key":"10.1002\/jps.2600771105_bb13","unstructured":"The solvents used for partitioning were mutually saturated with each other prior to use. This can avoid the change in their volume after partitioning"},{"key":"10.1002\/jps.2600771105_bb14","series-title":"Handbook of Chemistry and Physics","first-page":"C-365","author":"West","year":"1984"},{"key":"10.1002\/jps.2600771105_bb15","doi-asserted-by":"crossref","first-page":"1705","DOI":"10.1248\/cpb.15.1705","volume":"15","author":"Kakemi","year":"1967","journal-title":"Chem. Pharm. Bull. Japan"},{"key":"10.1002\/jps.2600771105_bb16","unstructured":"The \u0394log P values are the differences between the log Pcalc and log Pexp (\u0394log P = log Pcalc \u2212 log Pexp)"},{"key":"10.1002\/jps.2600771105_bb17","unstructured":"The partition coefficients were determined in 1-octanol\u2013water (pH 1.1) at 37\u00b0C. However, the partition coefficients for 5,5\u2013diethylbarbituric acid and 5-ethyl-5-phenylbarbituric acid at 37\u00b0C are essentially the same as those at 25\u00b0C (see text). Presumably, the temperature effect on partition coefficients of barbituric acids is small."},{"key":"10.1002\/jps.2600771105_bb18","series-title":"Quantitative Drug Design-A Critical Introduction","first-page":"184","author":"Martin","year":"1978"},{"key":"10.1002\/jps.2600771105_bb19","first-page":"1","volume":"6","author":"Tute","year":"1971","journal-title":"Adv. Drug Res."},{"key":"10.1002\/jps.2600771105_bb20","unstructured":"5-Isopropyl-5-phenylbarbituric acid has been synthesized and its log Pexp value has been determined in 1-octanol\u2013water to be 2.03."},{"key":"10.1002\/jps.2600771105_bb21","series-title":"Eton Four-Figure Mathematical and Statistical Tables","author":"Quinn","year":"1974"},{"key":"10.1002\/jps.2600771105_bb22","series-title":"Practical Organic Chemistry","first-page":"167","author":"Vogel","year":"1956"},{"key":"10.1002\/jps.2600771105_bb23","first-page":"250","volume":"1","author":"Adams","year":"1944","journal-title":"Org. Syn., Coll. Vol"},{"key":"10.1002\/jps.2600771105_bb24","doi-asserted-by":"crossref","first-page":"890","DOI":"10.1002\/recl.19260451205","volume":"45","author":"Backer","year":"1926","journal-title":"Rec. Trav. Chim."},{"key":"10.1002\/jps.2600771105_bb25","doi-asserted-by":"crossref","first-page":"1090","DOI":"10.1021\/ja01298a007","volume":"58","author":"Miller","year":"1936","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/jps.2600771105_bb26","first-page":"17612","volume":"57","year":"1957","journal-title":"Chem. Abst."},{"key":"10.1002\/jps.2600771105_bb27","first-page":"377","volume":"15","author":"Stuckey","year":"1942","journal-title":"Quart. J. Pharm. Pharmacol."},{"key":"10.1002\/jps.2600771105_bb28","doi-asserted-by":"crossref","first-page":"1078","DOI":"10.1021\/jm00318a020","volume":"10","author":"Beres","year":"1967","journal-title":"J. Med. Chem."},{"key":"10.1002\/jps.2600771105_bb29","doi-asserted-by":"crossref","first-page":"2949","DOI":"10.1021\/ja01108a048","volume":"75","author":"Bush","year":"1953","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/jps.2600771105_bb30","unstructured":"Chlorination of 5-t-butylbarbituric acid with sulfuryl chloride in dry chloroform and with chlorine in acetic acid was unsuccessful. This could be related to the slow ionization of the C5 proton of 5- t-butylbarbituric acid (ref 7)."},{"key":"10.1002\/jps.2600771105_bb31","unstructured":"We feel that the assignment of the carbon atom number for the phenyl group as 6 and for the allyl group as 3 needs to be revised since \u03c0Ph = 1.87 and \u03c0allyl = 1.35 both are smaller than the values (6 \u00d7 0.53 = 3.18) and (3 \u00d7 0.53 = 1.59), respectively. 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