主题:【已应助】两个有机化合物结构式 关于氢谱的疑问?

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haishinihao
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两个有机化合物结构式如下,且投了篇文章。审稿人给回复了关于氢谱的疑问,不明白审稿人的话是什么意思?大家帮我分析下。重谢!(另外说明下这两个化合物均为混旋体,未经拆分)。

Compound 1: Only one chemical shift for each proton in the COCH2-beta and NCH2 AB systems must be calculated. The first
chemical shift for the NCH2 AB system is not correct because calculation implies a coupling constant of 165 Hz.
Compound 1: Only one chemical shift for each proton in the NCH2 AB system must be calculated.
(我文章中写的)化合物1的数据:
1H NMR ( 500 MHz, CDCl3) δ: 2.47~2.57(m, 4H, 2×NCH2); 3.27~3.29(d, 1H, J=13.5Hz, COCH2-β); 3.41~3.44(d, 1H, J=13.5Hz, COCH2-α); 3.44~3.47(m, 4H, 2×OCH2); 4.10~4.43(d, J=15.5Hz, 1H, NCH2); 4.93~4.96(d, J=15.5Hz, 1H, NCH2); 5.75(s, 1H, furan-H20); 6.02(s, 1H, furan-H21); 7.68(s, 1H, furan-H22); 3.89(s, 3H, OCH3); 7.05(s, 1H, ArCH); 7.13~7.14(d, 2H, C6H5-H2,H6); 7.26~7.28(m, 1H, C6H5-H4); 7.35~7.37(m, 2H, C6H5-H3,H5); 7.37(s, 1H, quinoline ring-H7); 7.39(m, 1H, quinoline ring-H2); 7.65(m, 1H, quinoline ring-H3); 7.73(m, 1H, quinoline ring-H6).
化合物2的数据:
1H NMR ( 500MHz, CDCl3) δ:1.51~2.09(m, 15H, adamantyl group); 3.46(d, 1H, J=13.5Hz,COCH2-β); 3.74(d, 1H, J=13.5Hz, COCH2-α); 3.96(s, 3H, OCH3); 4.08~4.11(d, J=15.5Hz, 1H, NCH2); 4.99~5.02(d, J=15.5Hz, 1H, NCH2); 5.70(s, 1H, furan-H20); 6.03(s, 1H, furan-H19); 7.68(s, 1H, furan-H18); 7.09(s, 1H, ArCH); 7.15~7.16(d, 2H, C6H5-H2, H6); 7.30~7.32(m, 1H, C6H5-H4); 7.39~7.41(m, 2H, C6H5-H3, H5); 7.39(s, 1H, quinoline ring-H7); 7.41(m, 1H, quinoline ring-H2); 7.65(m, 1H, quinoline ring-H3); 7.73(m, 1H, quinoline ring-H6).
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wanglichao828
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关于4.10~4.43(d, J=15.5Hz, 1H, NCH2), 貌似耦合常数应该是(4.43-4.10)*500=165Hz是不是化学位移值搞错了;化合物2 中4.08~4.11(d, J=15.5Hz, 1H, NCH2); 4.99~5.02(d, J=15.5Hz, 1H, NCH2);是对的,你可以比较一下。
化合物1 中3.27~3.29(d, 1H, J=13.5Hz, COCH2-β); 3.41~3.44(d, 1H, J=13.5Hz, COCH2-α);和化合物2中3.46(d, 1H, J=13.5Hz,COCH2-β); 3.74(d, 1H, J=13.5Hz, COCH2-α);貌似表述不一致。个人觉得最好将3.27~3.29(d, 1H, J=13.5Hz, COCH2-β); 3.41~3.44(d, 1H, J=13.5Hz, COCH2-α);改为3.28(d, 1H, J=13.5Hz, COCH2-β); 3.43(d, 1H, J=13.5Hz, COCH2-α); 其他表述不一致的地方也需要改正。
个人觉得d峰表述是化学位移写成二个峰的平均值最好。
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