Heterocyclic Communications p. 215 - 222 (2005)
Update date:2022-07-29
Topics:
Tierney, John
Sheridan, Douglas
Mascavage, Linda
Gorbecheva, Daniela
Ripp, Michelle
Son, Sonjoo
A successful attempt has been made to predict 13C chemical shifts for a series of disubstituted 2,3-diphenyl-1,3-thiazolidin-4-ones. Prior work has shown that substituents placed on either phenyl ring of the 2,3-diphenyl-1,3-thiazolidin-4-one system affect the electron density surrounding the C-2, C-4 and C-5 atoms. These changes are reflected in the different nmr chemical shifts for these carbon atoms relative to the unsubstituted compound. The 13C chemical shifts for the C-2, C-4 and C-5 carbons of these compounds have previously been shown to correlate with Hammett σ constants and Swain Lupton dual substituent parameters. Because of these correlations we decided to investigate the potential for predicting 13C chemical shifts for C-2, C4 and C-5 in the thiazolidinone ring based on the known shifts for the two mono-substituted series of compounds. The effect of the substituents on the 13C chemical shifts for the C-2, C-4 and C-5 carbons in the disubstituted 2,3-diphenylthiazolidinones are discussed relative to the two mono-substituted 2,3-diphenylthiazolidinone series. The data is then used to predict the 13C chemical shift values at C-2, C-4 and C-5 in the thiazolidinone ring with all possible substituents combinations in the 2-phenyl and 3-phenyl rings.
Chongqing Rong＆Quan Pharmaceutical Technology Co. , Ltd.
Contact:86-023-65268721
Address:No. 7, Manshanhong Village, Pingdingshan, Shapingba District, Chongqing Province, China
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Contact:86-571-86737118-8689
Address:No.69, 12 Street, HEDA, Hangzhou, Zhejiang, China
Hefei EnliPharma Tecnology Co.,Ltd
Contact:0086-551-66399836
Address:Qing Cheng ShuiXiang Building 805, Mengcheng North Road , ShuangFeng Economic Development Zone Anhui HeFei
Contact:+86-25-52346955
Address:199,JIANYE ROAD,NANJING,CHINA
Doi:10.1016/S0040-4039(03)00456-8
(2003)Doi:10.1055/s-2003-36786
(2003)Doi:10.1039/jr9440000315
(1944)Doi:10.1016/S0040-4020(01)97349-1
(1974)Doi:10.1002/adsc.200900721
(2009)Doi:10.1021/acs.orglett.1c01300
(2021)
