What advice do you have for where to place the hyphen in a long word that wraps to the next line? For example, should the word “transformational” be hyphenated transform-ational or tranforma-tional? Is there a rule on that?
Well, I almost always let the application I’m using take care of my line breaks, and I almost always use ragged-right justification, rather than fully-justified paragraphs. That way, words almost never need to be broken between lines.
But since you asked, I pulled out my trusty copy of The Chicago Manual of Style (13th Edition*) to get their advice.
General principles. Most words should be divided according to pronunciation (the American system, reflected in Webster), not according to derivation (the British system):
democ-racy (not demo-cracy)
knowl-edge (not know-ledge)
aurif-erous (not auri-ferous)
antip-odes (not anti-podes)
It goes on from there to say that division should be made after a vowel unless that’s not exactly where the syllable break occurs, and that “two consonants standing between vowels are usually separated if the pronunciation warrants.”
Most importantly, they say that “words that have a misleading appearance when divided should be left unbroken if at all possible.”
So, let’s look at the syllables of your example word: Dictionary.com breaks it up this way:
So, using the “American system,” you could do it like this:
(I would avoid transformation-al; your readers would see the word transformation on one line, then jump down to the next line to be confronted with lonely little al, and be left scratching their heads.)
Chicago adds some more points about special cases like compound words, gerunds, prefixes and suffixes, and so on, so let me know if you need to know more.
Hope that helps.
*I really should get the latest edition; I’ve had this one since at least 1983 or ‘84.