D -Mannosamine hydrochloride (2-amino-2-deoxy- D -mannose hydrochloride): ionic hydrogen bonding in saccharides involving chloride and aminium ions
D -Mannosamine hydrochloride (2-amino-2-deoxy- D -mannose hydrochloride): ionic hydrogen bonding in saccharides involving chloride and aminium ions
复制标题
D-甘露糖胺盐酸盐（2-氨基-2-脱氧-D-甘露糖盐酸盐）：糖类中涉及氯离子和铵离子的离子氢键
DOI：
10.1107/s2053229622002121
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Serianni, Anthony S.
中科院分区：
文献类型：
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作者：
Lin, Jieye;Oliver, Allen G.;Serianni, Anthony S.
d-甘露糖胺盐酸盐（2-氨基-2-脱氧-d-甘露糖盐酸盐），C6 H14 NO 5+·Cl−，（I），在室温下从甲醇/乙酸乙酯/正己烷溶剂混合物中结晶，呈4C 1椅式构象，略微向C3，O 5 B型扭曲。比较了（I）与α-D-氨基葡萄糖盐酸盐（II）和β-D-氨基半乳糖盐酸盐（III）/（III′）的结构参数，以评价离子氢键对结构性质的影响。在（I）-（III）/（III′）晶体中存在三种类型的离子氢键，即N+-H <$O、N+-H <$Cl−和O-H <$Cl−。在（I），（II）和（III）/（III′）中的环外结构参数似乎受这种键合的影响最大，特别是环外羟基，其采用通过离子氢键与氯阴离子实现的重叠构象。在（I）的晶体中观察到异头无序，α：β比为37：63。然而，端基异构体的配置似乎施加最小的结构影响，也就是说，键长，键角和扭转角是基本相同的两个端基异构体。在异头C原子（I）观察到的障碍似乎是由氯阴离子和原子O3或O 4在近端空隙的存在下，这提供了在轴向和赤道方向上的氢键原子O 1的机会。
d-Mannosamine hydrochloride (2-amino-2-deoxy-d-mannose hydrochloride), C6H14NO5+·Cl−, (I), crystallized from a methanol/ethyl acetate/n-hexane solvent mixture at room temperature in a 4C1 chair conformation that is slightly distorted towards the C3,O5B form. A comparison of the structural parameters of (I) with the corresponding parameters in α-d-glucosamine hydrochloride, (II), and β-d-galactosamine hydrochloride, (III)/(III′), was undertaken to evaluate the effects of ionic hydrogen bonding on structural properties. Three types of ionic hydrogen bonds are present in the crystals of (I)–(III)/(III′), i.e. N+—H⋯O, N+—H⋯Cl−, and O—H⋯Cl−. The exocyclic structural parameters in (I), (II), and (III)/(III′) appear to be most influenced by this bonding, especially the exocyclic hydroxy groups, which adopt eclipsed conformations enabled by ionic hydrogen bonding to the chloride anion. Anomeric disorder was observed in crystals of (I), with an α:β ratio of 37:63. However, anomeric configuration appears to exert minimal structural effects; that is, bond lengths, bond angles, and torsion angles are essentially identical in both anomers. The observed disorder at the anomeric C atom of (I) appears to be caused by the presence of the chloride anion and atom O3 or O4 in proximal voids, which provide opportunities for hydrogen bonding to atom O1 in both axial and equatorial orientations.