CONFORMATIONAL ANALYSIS IN SATURATED HETEROCYCLIC COMPOUNDS
CONFORMATIONAL ANALYSIS IN SATURATED HETEROCYCLIC COMPOUNDS
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DOI：
10.1021/ar50025a001
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发表时间：
1970-01-01
影响因子：
18.3
通讯作者：
ELIEL, EL
中科院分区：
文献类型：
--
作者：
ELIEL, EL
构象分析是指根据相应分子的基态、过渡态或激发态的“构象”(围绕单键的旋转排列)来分析化合物的物理化学性质。虽然构象分析历史上可以追溯到Sachse1关于环己烷的椅子和柔性(船)形式的经典论文，但今天这一主题的广泛影响是由Barton23的开创性论文开创的，他将环己烷的构象与稳定性、物理性质和反应性联系起来。在过去的12年里，从构象的角度对环己烷和(程度较小的)简单烷烃8·4567进行了定量和定性的研究，并提供了这一领域广泛的信息的几个摘要。5-8许多重要的环状化合物--碳水化合物、许多生物碱、核酸，甚至四氢大麻酚--以及大多数非环化合物(包括聚甲醛和聚氧乙烯等聚合物)含有碳和氢以外的元素，这一事实表明有必要将构象研究扩大到具有杂原子的环和链。虽然定性研究，特别是在生物碱和碳水化合物领域的研究是可用的(在碳水化合物的情况下，有时先于对碳环的类似研究)9和尽管质子磁共振应用的一些开创性工作已经在碳水化合物中。
By conformational analysisis meantthe analysis of physical and chemical properties of compounds in terms of the “conformation”(rotational arrangement about single bonds) of the ground states, transition states, or excited states of the corresponding molecules. While conformational analysis historically dates back to the classical paperof Sachse1 on the chair and flexible (boat) forms of cyclohexane, the wide impact of the sub-ject today was initiated by the pioneering paper of Barton2 3relating cyclohexane conformation to stability, physical properties, and reactivity. In the past 12 years cyclohexane and (to a lesser extent) simple al-kanes8· 4 567have been studied quantitatively as well as qualitatively fromthe conformational point of view, and several summaries of the extensive body of information in thisfield are available. 5-8The fact that many important cyclic compounds—carbohydrates, many alkaloids, nucleic acids, and even tetrahydrocannabinol—as well as the majority of acy-clic compounds (including polymers such as polyoxymethylene and polyoxyethylene) contain elements other than carbon and hydrogen demonstrates the need for extending conformational study to rings and chains with heteroatoms. Although qualitative studies, es-pecially in the alkaloid and carbohydrate area, are available (and, in the case of carbohydrates, sometimes have preceded similar studies in carbocycles) 9 and al-though some of the pioneering work in the application of proton magnetic resonance has been in the carbohy-