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Dots, dashes and hydrogen bonds

机译:点,破折号和氢键

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摘要

Hydrogen bonding is undoubtedly the most widely appreciated non-covalent interaction in chemical and biological systems. Although classified as a 'weak interaction' in textbooks, hydrogen bonding is central to molecular recognition, supramolecular assembly and self-organization in solutions and in crystals. As inveterate readers of the chemical literature, we noticed that there is no uniform notation for representing hydrogen bonds in chemical structures. Publishers like the American Chemical Society, Wiley--VCH, Springer Verlag use a three-dot (...) convention for denoting a hydrogen bond (X-H...Y) in running text. However, some journals and most textbooks do not appear to use this representation, uniformly. Hydrogen bonds appear as solid lines (disguised covalency?) in the Journal of Chemical Physics, although another article in the same journal uses the comforting three-dot notation. The Journal of Physical Chemistry represents hydrogen bonding by three dots in the running text, but succumbs to a single solid line in the title3. The Journal of Biological Chemistry appears to approve of two dots to represent hydrogen bonds in the running text4. Four dot hydrogen bonds appear in the widely used text, Advanced Organic Chemistry by March5, an aberration duly corrected to three dots in the fifth edition of March's Advanced Organic Chemistry6. Organic Chemistry by Finar7 uses two dashes (...). In consulting colleagues on the dots, dashes and the significance of their numbers for hydrogen bonds, we realized that this notation may not have been formally used by the International Union of Pure and Applied Chemistry (IUPAC) and that no decrees exist. In reflecting on dots, we note that, two dots vertically arranged represent the covalent bond; a formalism that evolved while G. N. Lewis lectured to undergraduates at Berkeley. Alfred Werner anticipated the three-dot notation, although he used this notation to represent an electrostatic interaction between a proton donor and ammonia, X(H...NH_3). Maurice Muggins appears to have been among the earliest to use three dots for hydrogen bonds (bridges, at that time). Two years later, Linus Pauling institutionalized the three-dot representation in his now classic book The Nature of the Chemical Bond. Interestingly, many journals and authors appear to have followed this convention (possibly unconsciously), while others seem to have been free to experiment. May be in the not-too-distant future we will see the recommendation of a committee that considers how many dots and dashes make a hydrogen bond.
机译:氢键无疑是化学和生物系统中最广为人知的非共价相互作用。尽管在教科书中被归类为“弱相互作用”,但氢键对于溶液和晶体中的分子识别,超分子组装和自组织至关重要。作为化学文献的资深读者,我们注意到在化学结构中没有统一的符号表示氢键。诸如美国化学学会,Wiley-VCH,Springer Verlag之类的出版商使用三点(...)约定在运行文本中表示氢键(X-H ... Y)。但是,某些期刊和大多数教科书似乎并没有统一使用这种表示形式。氢键在《化学物理学》杂志上以实线(伪称共价?)出现,尽管同一期刊上的另一篇文章使用了令人愉悦的三点符号。 《物理化学杂志》在正文中用三个点表示氢键,但在标题中屈服于一条实线。 《生物化学杂志》似乎赞成两个点代表运行文本中的氢键4。在广泛使用的文章“ 3月5日的高级有机化学”中出现了四个点的氢键,该象差在3月的第五版“高级有机化学” 6中已正确校正为三个点。 Finar7撰写的有机化学使用两个破折号(...)。在向同事咨询点,破折号及其氢键数字的意义时,我们意识到国际纯净与应用化学联合会(IUPAC)可能尚未正式使用此表示法,并且不存在任何法令。在点上反射时,我们注意到,垂直排列的两个点代表共价键;在G. N. Lewis向伯克利大学的本科生讲课时演变而来的一种形式主义。阿尔弗雷德·沃纳(Alfred Werner)预计使用三点表示法,尽管他使用该表示法表示质子供体与氨X(H ... NH_3)之间的静电相互作用。莫里斯·麦金斯(Maurice Muggins)似乎是最早使用三个点进行氢键(当时为桥)的人。两年后,莱纳斯·鲍林(Linus Pauling)在他现在经典的《化学键的性质》一书中将三点表示法制度化。有趣的是,许多期刊和作者似乎遵循了这一惯例(可能是无意识的),而其他期刊和作者似乎可以自由地进行试验。也许在不久的将来,我们将看到一个委员会的建议,该委员会考虑多少个点和破折号构成氢键。

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