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In many old chemistry books there were limitations on how chemical structures could be represented driven, presumably, by the desire to use available typesetting methods to save costs.

For example, this is a page from a book on industrial chemicals published in the 1930s:

Image from Industrial Chemistry vol II, by Allen Rogers, Macmillian, 5th Ed. 1931

The distorted hexagons are 6-membered aromatic rings but are typeset from vertical and 45° lines with none of the double bonds explicitly shown.

When and how did chemical typesetting become more "realistic" with, for example, proper hexagons for aromatic rings and the correct description of double bonds where appropriate?

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  • $\begingroup$ Is this helpful? researchgate.net/figure/… $\endgroup$ – user55119 Mar 23 '18 at 22:02
  • $\begingroup$ Your example looks like lead typesetting and apparently was limited by the available type sorts. $\endgroup$ – Loong Mar 24 '18 at 12:22
  • $\begingroup$ @Loong I'm fairly sure you are right. I wonder whether anyone has compiled a typographic history of chemistry? $\endgroup$ – matt_black Mar 24 '18 at 12:28
  • $\begingroup$ @user55119 An interesting collection of relatively recent examples. Interesting, but I'd love to see a spread of examples over a century. $\endgroup$ – matt_black Mar 24 '18 at 12:31
  • $\begingroup$ In that case, you may be interested in Henry Rzepa's blog (split over multiple posts). $\endgroup$ – pentavalentcarbon Mar 24 '18 at 19:32
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this isn't a definite answer but it might show the direction:

I have an old copy of Namensreaktionen in der Organischen Chemie, 2nd ed. by Helmut Krauch and Werner Kunz, published in 1962 at Alfred Hüthig. First edition must have been published in 1960 or 1961.

Mechanism of the Bischler-Napieralski ring closure

Most of the arenes in the sketches have the proper shape. Once in a while they seem to be deliberately stretched to align centres that react.

All through the book there's a consistent notation for saturated centres, hydrogen atoms are mostly not omitted.

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  • $\begingroup$ Looks like a similar typesetting process to my example but with more effort to get the correct unsaturation. Also an odd mix of elongated and correctly proportioned hexagons. $\endgroup$ – matt_black Mar 24 '18 at 12:27
  • $\begingroup$ @matt_black You're right. I copied this figure on purpose. Seem it was their way to indicate that "the carbocation goes there"without using curved arrows which probably weren't available. Other hexagons in the book are mostly correct. $\endgroup$ – Klaus-Dieter Warzecha Mar 24 '18 at 12:46

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