首页> 外文期刊>Spectroscopy Letters >Stereochemical effects on H-1 chemical shifts in 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH), 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) and related molecules
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Stereochemical effects on H-1 chemical shifts in 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH), 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) and related molecules

机译:立体化学对2,3-二氮杂双环[2.2.1]庚-2-烯(DBH),2,3-二氮杂双环[2.2.2] oct-2-ene(DBO)和相关分子中H-1化学位移的影响

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摘要

H-1-NMR spectra of DBH (1), DBO (2) and of the synthetic precursor to 1, 1,4-phenyl-2,4,6-triazatricyclo[5.2.1.0(2,6)]heptane-3,5-dione (5), were recorded in acetone-d(6) and C6D6 at 500 MHz. Assignment was aided by complete resolution of signals of 1 and 2 in C6D6 by aromatic solvent-induced shifts (ASIS). The effect of the change fi om phenyltriazolinedione to a diazene functional group on the chemical shifts of the exo,endo and syn,anti protons was investigated. The chemical shifts of the exo,endo protons of 1 are exceptionally sensitive to the functional group at the heterosubstituted bridge in the DBH skeleton. However, the relative chemical shift of the syn,anti proton pair is independent of the nature of the functional group. The role of stereochemical effects on these chemical shifts is discussed. [References: 21]
机译:DBH(1),DBO(2)以及1,,4-苯基-2,4,6-三氮杂三环[5.2.1.0(2,6)]庚烷-3的合成前体的H-1-NMR光谱在丙酮-d(6)和C6D6中于500 MHz记录了1,5-二酮(5)。通过芳族溶剂诱导的位移(ASIS)完全解析C6D6中1和2的信号有助于分配。研究了由苯基三唑啉二酮向重氮官能团的变化对外,内,顺,反质子的化学位移的影响。 1的内,外质子的化学位移对DBH骨架中杂取代桥键上的官能团异常敏感。但是,顺反质子对的相对化学位移与官能团的性质无关。讨论了立体化学作用对这些化学位移的作用。 [参考:21]

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