If you have a nail or anything else that punctures the sidewall of your tire, you have to get a new tire. This part of the tire doesn't have the same structure as the tread area and needs to be intact to be safe. A patch or a plug are both good ideas for many kind of tires, but only if the nail or puncture is in the main portion of the tread and not too close to the sidewall. Generally it is felt that as long as the nail is not within the last inch of tread on either side it should be safe to be repaired. However if you get something in the sidewall of your car tire like the picture shows, this means you should get a new one. There are many factors that should be considered when a tire is damaged as to whether the tire can be replaced or repaired. (Off road and commercial tires are a different design and can be patched more often than passenger tires)

More Info: www.tireindustry.org