ENCODING AND DECODING HYDROGEN-BOND PATTERNS OF ORGANIC-COMPOUNDS
ENCODING AND DECODING HYDROGEN-BOND PATTERNS OF ORGANIC-COMPOUNDS
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DOI：
10.1021/ar00172a005
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发表时间：
1990-04-01
影响因子：
18.3
通讯作者：
ETTER, MC
中科院分区：
文献类型：
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作者：
ETTER, MC
氢键模式是可预测的吗？苯甲酸形成环状二聚体。水杨酸具有分子内氢键。这些氢键模式似乎是显而易见的，因为它们满足了一个有点酸性的氢与一个电负性原子配对的化学标准，而且因为光谱学和晶体学研究已经证实了我们关于氢键在这些结构中以及在类似的经常研究的结构中如何以及何时形成的化学直觉。[1]但是其他研究较少的简单化合物，如二乙酰胺，又如何呢？二乙酰胺有两个质子受体、一个质子供体和三种可能的构象异构体，每种构象异构体都能形成两个或三个中心的氢键链或二聚体。四个氢键的可能性显示。模式1和3在二乙酰胺的两种多晶型物中发现。[2]除了这些模式，二乙酰胺还与许多其他氢键分子共结晶。[3]进行这种预测的内在复杂性在复杂的氢键模式中显而易见。
Are hydrogen-bond patterns predictable? Benzoic acids form cyclic dimers. Salicylic acid has an intra-molecular hydrogen bond. These hydrogen-bond pat-terns seem obvious because they satisfy the chemical criteria of pairing a somewhat acidic hydrogen with an electronegative atom, and because spectroscopic and crystallographic studies have confirmed our chemical intuition about how and when hydrogen bonds should form in these and in similar frequently studied struc-tures. 1 But what about other, less studied, yet simple compounds like diacetamide? Diacetamide has two proton acceptors, one proton donor, and threepossible conformers each of which could form two-or threecentered hydrogen-bonded chains or dimers. Four of the hydrogen-bond possibilities are shown. Patterns 1 and 3 are found in the two polymorphs of diacetamide. 2 Besides these patterns, diacetamide also cocrystallizes with many other hydrogen-bonding molecules. 3 The inherent complexities in making such predictions are apparent in the intricate hydrogen-bond pattern ob-/' o o-o o i i