Why can I not open a file in lightroom to an external editor?

I have recently restored my photo library on an external drive via time machine and all has been good. Now I have updated lightroom to 4.4 and cannot open any files to an external editor... photoshop cs4 or any nik software program. I am running OS X.6.8. Any ideas as to what has happened and how to fix?
It comes up with "Lightroom was unable to prepare the selected file at.... for editing. It will not be opened."

Not sure what the problem is..... When I originalte an email, or reply to one, I have the paperclip icon that I use to attatch files that need to be sent.
Do you not have the paperclip icon?  If not, when you initiate a new outgoing email, go to the VIEW menu, and make sure Show Toolbar is checked....

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