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Prior to the development of the な particle (presumably from なる) several hundred years ago, what constructions were used where な-construtions are currently used? E.g. in the phase きれいな女, would that have been きれいの女, 女のきれい, きれい女 (and would that be kireionna or kirei onna?), きれいなる女 or something else?

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I think that なる is used. –  user54609 Feb 1 at 20:39
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なり and たり conjugate like ラ変 verbs. –  Zhen Lin Feb 2 at 1:51
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「きれいな女」の「な」って、助詞なの? –  Chocolate Feb 2 at 15:58
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@Chocolate 助詞というより助動詞かな? –  Zhen Lin Feb 2 at 18:25
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Sorry, are you asking what developed into なる, or what developed into な? –  dainichi Feb 3 at 1:17
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up vote 3 down vote accepted

It is from なる, in a way; but it may not be the one you're thinking of. The なる here is the 連体形 of the former copula なり, which itself derives from に+あり (modern ある). This seems to have been the copula as far back as we have records of. Indeed, this kind of adjective is younger than the copula it uses - these kinds of adjectives do not occur before the Heian-jidai.

A couple of forms do appear that have since become them (e.g. adjectives ending in -らか), but I don't know how these were used - my source (Bentley's Descriptive Grammar of Old Japanese Prose) mentions their existence, but only says that these なり-based adjectives are new as of the Heian-jidai; it says nothing at all about how they were used in Old Japanese. I would speculate that they're used in the very old adjective patterns that require no morphology at all: so just like you can get /awo sora/ (/səra/?) where you would expect /awo-ki sora/, I bet you could get /tapiraka umi/ when later you would expect /taɸiraka=naru umi/ (for 平らかな海).

As for きれい, it's a Chinese loanword, and was loaned after the creation of these kinds of adjectives. So there was never a point in time before きれいなる女 - you would have used a native Japanese word like 美しい, and so you would have either /utukusi-ki womina/ or the older /utukusi womina/.

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