The leak is probably because the o-ring you have is the green hi-nitrile type. The green o-rings are harder than the black ones. The green ones are more scuff resistant and can tolerate higher temperatures than the black ones I think too. For sealing air, you normally would use the black ones because they are softer and squish into gaps to seal the air. All of the air-sealing o-rings on my fx maverick are the black ones. Technically, I think you can find black ones that are also as hard as the green ones, but I've never seen a green one that was not the extra hard kind. Bottom line is that you don't want the hard o-ring for making that seal. I think you want buna 70 hardness (black ones generally), not buna 90 which you appear to have.
grungy