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What is the rule that you have to follow to be able to use 's instead of is?

For example, you can say Jill's very happy, but you can't say However happy Jill's I'd still like to tell her another joke.

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This question is related to the question raised in english.stackexchange.com/questions/105910/…. I think that this one stands on its own, however. – Sven Yargs Mar 5 '13 at 3:53
Yeah. You can't use the contraction at the end of a clause. The word at the end of the clause is stressed, and you can't stress a suffix, so you have to stress is and can't contract it. – John Lawler Mar 5 '13 at 4:05

As per John Lawler's comment,

You can't use a contraction at the end of a clause.
The word at the end of the clause "However happy Jill's" is stressed, and you can't stress a suffix,
so you have to stress "is" and thus can't contract it.

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As John Lawler said in the comments, contractions should be avoided at the end of a clause because it creates two conflicting stresses. However, to expand on his fine answer, speech should be phrased in such a way that it doesn't sound awkward to the speaker or listener (or writer and reader).

This problem doesn't have a hard and fast rule, or at least, none that I've ever seen in my studies. Nor would I expect to find one on a subject like this, except perhaps in an English as a second language textbook. However, this does fall under a blanket rule of all language: the purpose of language is to facilitate effective communication.

Basically, if a phrase sounds like it would be unable to communicate an idea, or if it would unintentionally break the flow of communication, then reword it. In your case, 'However happy Jill's...' doesn't work because of the stress problem that Mr. Lawler mentioned. In addition, that structure is such that a listener or reader would expect the 's to be be possessive; 'However happy Jill's friend is...' would flow well, despite having exactly the same initial words. Much of language is anticipation (as demonstrated by compression techniques used for text), and subverting that anticipation should be done with care and deliberation.

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